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CAS 108-24-7
Acetic acid acetic anhydrideacetic anhydrideAcetic anhydride
Codes: (XXXI)1024528-1-c, (XXIV)101438-13-c, (II)101438-43-a, (III)101438-51-a, (II)101438-58-a, (XV)101438-71-b,(XV)101438-71-c, (XVI)101438-72-b, (II)101438-77-a, FLUTI-022, S-pantoprazole sodium-026, Ketoconazole-012, (XVI)443746-1-c +1 more
Application context (from source-drug indications)
Non-small cell lung cancerPralsetinibThyroid cancerPralsetinibMedullary thyroid cancerPralsetinibBreast cancerPaclitaxel/Encequidar mesylateAdenocarcinomaPaclitaxel/Encequidar mesylateAngiosarcomaPaclitaxel/Encequidar mesylateSolid tumourPaclitaxel/Encequidar mesylateAsthmaFluticasone Propionate/Formoterol Fumarate HydrateChronic obstructive pulmonary diseaseFluticasone Propionate/Formoterol Fumarate HydrateGastro-oesophageal reflux diseaseS-pantoprazole sodiumPeptic ulcerS-pantoprazole sodiumHaemorrhageS-pantoprazole sodiumTrauma and injuryS-pantoprazole sodiumComaS-pantoprazole sodiumAspiration pneumoniaS-pantoprazole sodiumFungal infectionNaftifine hydrochloride/KetoconazolePancreatic cancerPaclitaxelNon-small cell lung cancerPaclitaxelHodgkin's diseasePaclitaxelSeminomaPaclitaxelOvarian cancerPaclitaxelBreast cancerPaclitaxelNasal congestionFluticasone PropionateAllergic rhinitisFluticasone Propionate鼻息肉Fluticasone PropionateRhinitisFluticasone Propionate扁平苔藓Fluticasone PropionateRashFluticasone PropionateCushing's syndromeKetoconazole头皮屑KetoconazolePityriasis versicolorKetoconazole皮肤念珠菌病KetoconazoleTineaKetoconazole脂溢性皮炎Ketoconazole下丘脑肥胖Setmelanotide Acetate巴德特-别德尔综合征Setmelanotide AcetateObesitySetmelanotide AcetatePrader-Willi综合征Setmelanotide Acetate垂体疾病Setmelanotide Acetate联合性垂体激素缺乏症Setmelanotide AcetateHypercalcaemiaCinacalcet HydrochlorideSecondary hyperparathyroidismCinacalcet HydrochlorideHyperparathyroidismCinacalcet HydrochloridePrimary hyperparathyroidismCinacalcet HydrochlorideChronic renal impairmentCinacalcet HydrochlorideCardiogenic oedemaCinacalcet Hydrochloride
Source drugs (routes using this intermediate)
| Drug | Tier | Expiry |
|---|---|---|
| Pralsetinib | Tier C — Watch / trade | 2031 |
| Paclitaxel/Encequidar mesylate | Tier C — Watch / trade | - |
| Fluticasone Propionate/Formoterol Fumarate Hydrate | Tier C — Watch / trade | - |
| S-pantoprazole sodium | Tier C — Watch / trade | - |
| Naftifine hydrochloride/Ketoconazole | Tier C — Watch / trade | - |
| Paclitaxel | Tier B — Position early | - |
| Fluticasone Propionate | Tier B — Position early | - |
| Ketoconazole | Tier C — Watch / trade | - |
| Setmelanotide Acetate | Tier C — Watch / trade | - |
| Cinacalcet Hydrochloride | Tier B — Position early | - |
Position in synthesis routes (up/downstream chain)
Ordered by route registration; left → right is the synthesis direction. The highlighted node is the current CAS; others link to their own profiles.
1-[6-(4-Fluoro-1H-pyrazol-1-yl)pyridin-3-yl]ethan-1-one→4-Fluoro-1H-pyrazole→2,2,3,3-Tetrafluoropropan-1-ol→4-(2,2,3,3-Tetrafluoropropyl)morpholine→4-Methyl-4-(2,2,3,3-tetrafluoropropyl)morpholin-4-ium mesylate→1,2-Diazole→4-Methyl-4-[(1Z)-2,3,3-trifluoroprop-1-en-1-yl]morpholin-4-ium methanesulfonate→(2Z)-2-Fluoro-3-(morpholin-4-yl)prop-2-enal→Hydrazine dihydrochloride→4-Fluoro-1H-pyrazole hydrogen chloride→5-Bromo-2-chloropyridine→Acetic acid acetic anhydride→1-(6-Chloropyridin-3-yl)ethanone
(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-Bis(acetyloxy)-1,15-dihydroxy-10,14,17,17-tetramethyl-11-oxo-9-[(triethylsilyl)oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate→(3aS,9aS,10S,11aR,13aS,13bR,13cS)-13a-Hydroxy-6,9a,14,14-tetramethyl-10-[(triethylsilyl)oxy]-4,5,9a,10,11,11a,13,13a,13b,13c-decahydro-3a,7-methano[1,3]dioxolo[9,10]cyclodeca[1,2-d][1]benzoxete-2,8(9H)-dione→Acetic acid acetic anhydride→(2alpha,5beta,7beta,9beta,10beta)-4,10-Diacetoxy-1,9-dihydroxy-7-[(triethylsilyl)oxy]-5,20-epoxytax-11-en-2-yl benzoate→(3aS,9aS,10S,11aR,13aS,13bR,13cS)-6,9a,14,14-Tetramethyl-2,8-dioxo-10-[(triethylsilyl)oxy]-4,5,8,9,9a,10,11,11a,13b,13c-decahydro-3a,7-methano[1,3]dioxolo[9,10]cyclodeca[1,2-d][1]benzoxet-13a(13H)-yl acetate→Lithiumbenzene→(2alpha,5beta,7beta)-4-Acetoxy-1-hydroxy-10-oxo-7-[(triethylsilyl)oxy]-5,20-epoxytax-11-en-2-yl benzoate→(2alpha,5beta,7beta,9beta)-4-Acetoxy-1,9-dihydroxy-10-oxo-7-[(triethylsilyl)oxy]-5,20-epoxytax-11-en-2-yl benzoate
(2alpha,5beta,7beta,10beta,13alpha)-4-(Acetyloxy)-1,7,10,13-tetrahydroxy-9-oxo-5,20-epoxytax-11-en-2-yl benzoate→Acetic acid acetic anhydride→(2alpha,5beta,7beta,10beta,13alpha)-4,10-Bis(acetyloxy)-1,7,13-trihydroxy-9-oxo-5,20-epoxytax-11-en-2-yl benzoate→(2alpha,5beta,7beta,10beta,13alpha)-4,10-Bis(acetyloxy)-1,13-dihydroxy-9-oxo-7-[[(2,2,2-trichloroethoxy)carbonyl]oxy]-5,20-epoxytax-11-en-2-yl benzoate→(3R,4S)-1-Benzoyl-4-phenyl-3-(triethylsiloxy)azetidin-2-one→(2alpha,5beta,7beta,10beta,13alpha)-4,10-Bis(acetyloxy)-1-hydroxy-9-oxo-13-([(2R,3S)-3-phenyl-3-[(phenylcarbonyl)amino]-2-[(triethylsilyl)oxy]propanoyl]oxy)-7-[[(2,2,2-trichloroethoxy)carbonyl]oxy]-5,20-epoxytax-11-en-2-yl benzoate
(2alpha,5beta,7beta,10beta,13alpha)-4-(Acetyloxy)-13-[[(2R,3S)-3-benzamido-2-hydroxy-3-phenylpropanoyl]oxy]-1,7,10-trihydroxy-9-oxo-5,20-epoxytax-11-en-2-yl benzoate→(2alpha,5beta,7beta,10beta,13alpha)-4-(Acetyloxy)-1,10-dihydroxy-9-oxo-13-([(2R,3S)-3-phenyl-3-[(phenylcarbonyl)amino]-2-[(triethylsilyl)oxy]propanoyl]oxy)-7-[(triethylsilyl)oxy]-5,20-epoxytax-11-en-2-yl benzoate→Acetic acid acetic anhydride→(2alpha,5beta,7beta,10beta,13alpha)-4,10-Bis(acetyloxy)-1-hydroxy-9-oxo-13-([(2R,3S)-3-phenyl-3-[(phenylcarbonyl)amino]-2-[(triethylsilyl)oxy]propanoyl]oxy)-7-[(triethylsilyl)oxy]-5,20-epoxytax-11-en-2-yl benzoate
(2alpha,5beta,7beta,10beta,13alpha)-4-(Acetyloxy)-1,7,10,13-tetrahydroxy-9-oxo-5,20-epoxytax-11-en-2-yl benzoate→Acetic acid acetic anhydride→(2alpha,5beta,7beta,10beta,13alpha)-4,10-Bis(acetyloxy)-1,7,13-trihydroxy-9-oxo-5,20-epoxytax-11-en-2-yl benzoate→(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-Bis(acetyloxy)-1,15-dihydroxy-10,14,17,17-tetramethyl-11-oxo-9-[(triethylsilyl)oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate→(2R,4S,5R)-2-(4-Methoxyphenyl)-4-phenyl-3-[(prop-2-en-1-yloxy)carbonyl]-1,3-oxazolidine-5-carboxylic acid→5-[(2alpha,5beta,7beta,10beta,13alpha)-4,10-Bis(acetyloxy)-2-(benzoyloxy)-1-hydroxy-9-oxo-7-[(triethylsilyl)oxy]-5,20-epoxytax-11-en-13-yl] 3-prop-2-en-1-yl (2R,4S,5R)-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-3,5-dicarboxylate→5-[(2alpha,5beta,7beta,10beta,13alpha)-4,10-Bis(acetyloxy)-2-(benzoyloxy)-1,7-dihydroxy-9-oxo-5,20-epoxytax-11-en-13-yl] 3-prop-2-en-1-yl (2R,4S,5R)-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-3,5-dicarboxylate→(2alpha,5beta,7beta,10beta,13alpha)-4,10-Bis(acetyloxy)-2-(benzoyloxy)-1,7-dihydroxy-9-oxo-5,20-epoxytax-11-en-13-yl (2R,4S,5R)-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylate
(1S,5S,10S,11S,12S,16S)-10-(Benzyloxy)-7,11,14,14,18,21,21-heptamethyl-2,4,13,15-tetraoxapentacyclo[15.3.1.0(1,5).0(6,11).0(12,16)]henicosa-6,17-dien-3-one→(3aS,5S,8R,9aS,10S,13bS)-5-Hydroxy-6,9a,13,14,14-pentamethyl-12-[2-(4-methylbenzene-1-sulfonyl)hydrazinylidene]-2,9-dioxo-10-[(triethylsilyl)oxy]-5,8,9,9a,10,11,12,13b-octahydro-2H,4H-3a,7-methanobenzo[3,4]cyclodeca[1,2-d][1,3]dioxol-8-yl acetate→(3aS,5S,8R,9aS,10S,13bS)-6,9a,13,14,14-Pentamethyl-12-[2-(4-methylbenzene-1-sulfonyl)hydrazinylidene]-2,9-dioxo-10-[(triethylsilyl)oxy]-5-[(trimethylsilyl)oxy]-5,8,9,9a,10,11,12,13b-octahydro-2H,4H-3a,7-methanobenzo[3,4]cyclodeca[1,2-d][1,3]dioxol-8-yl acetate→(3aS,8R,9aS,10S,13bS)-10-(Benzyloxy)-6,9a,13,14,14-pentamethyl-2,9-dioxo-5,8,9,9a,10,11,12,13b-octahydro-2H,4H-3a,7-methanobenzo[3,4]cyclodeca[1,2-d][1,3]dioxol-8-yl acetate→(3aS,8R,9aS,10S,13bS)-6,9a,13,14,14-Pentamethyl-2,5,9,12-tetraoxo-10-[(triethylsilyl)oxy]-5,8,9,9a,10,11,12,13b-octahydro-2H,4H-3a,7-methanobenzo[3,4]cyclodeca[1,2-d][1,3]dioxol-8-yl acetate→(3aS,8R,9aS,10S,13bS)-6,9a,13,14,14-Pentamethyl-2,9-dioxo-10-[(triethylsilyl)oxy]-5,8,9,9a,10,11,12,13b-octahydro-2H,4H-3a,7-methanobenzo[3,4]cyclodeca[1,2-d][1,3]dioxol-8-yl acetate→(3aS,8S,9S,9aR,10S,13bS)-10-(Benzyloxy)-8,9-dihydroxy-6,9a,13,14,14-pentamethyl-5,8,9,9a,10,11,12,13b-octahydro-2H,4H-3a,7-methanobenzo[3,4]cyclodeca[1,2-d][1,3]dioxol-2-one→(3aS,8S,9S,9aR,10S,13bS)-10-(Benzyloxy)-9-hydroxy-6,9a,13,14,14-pentamethyl-2-oxo-5,8,9,9a,10,11,12,13b-octahydro-2H,4H-3a,7-methanobenzo[3,4]cyclodeca[1,2-d][1,3]dioxol-8-yl acetate→4-Methylbenzenesulfonhydrazide→Acetic acid acetic anhydride
Acetic acid acetic anhydride→(3aS,5S,8R,9aS,10S,13bS)-6,9a,13,14,14-Pentamethyl-12-[2-(4-methylbenzene-1-sulfonyl)hydrazinylidene]-2,9-dioxo-10-[(triethylsilyl)oxy]-5-[(trimethylsilyl)oxy]-5,8,9,9a,10,11,12,13b-octahydro-2H,4H-3a,7-methanobenzo[3,4]cyclodeca[1,2-d][1,3]dioxol-8-yl acetate→(3aS,5S,8R,9aS,10S,13aR,13bS)-6,9a,13,14,14-Pentamethyl-2,9-dioxo-10-[(triethylsilyl)oxy]-5-[(trimethylsilyl)oxy]-5,8,9,9a,10,11,13a,13b-octahydro-2H,4H-3a,7-methanobenzo[3,4]cyclodeca[1,2-d][1,3]dioxol-8-yl acetate→(3aS,5S,8R,9aS,10S,12S,13aR,13bS)-12-Hydroxy-6,9a,14,14-tetramethyl-13-methylidene-2,9-dioxo-10-[(triethylsilyl)oxy]-5-[(trimethylsilyl)oxy]-5,8,9,9a,10,11,12,13,13a,13b-decahydro-2H,4H-3a,7-methanobenzo[3,4]cyclodeca[1,2-d][1,3]dioxol-8-yl acetate→(3R,4S)-1-Benzoyl-4-phenyl-3-(triethylsiloxy)azetidin-2-one→(3aS,5S,8R,9aS,10S,12S,13aR,13bS)-12-[(Methanesulfonyl)oxy]-6,9a,14,14-tetramethyl-13-methylidene-2,9-dioxo-10-[(triethylsilyl)oxy]-5-[(trimethylsilyl)oxy]-5,8,9,9a,10,11,12,13,13a,13b-decahydro-2H,4H-3a,7-methanobenzo[3,4]cyclodeca[1,2-d][1,3]dioxol-8-yl acetate→(3aS,5S,8R,9aS,10S,12S,13S,13aR,13bS)-13-Hydroxy-13-(hydroxymethyl)-12-[(methanesulfonyl)oxy]-6,9a,14,14-tetramethyl-2,9-dioxo-10-[(triethylsilyl)oxy]-5-[(trimethylsilyl)oxy]-5,8,9,9a,10,11,12,13,13a,13b-decahydro-2H,4H-3a,7-methanobenzo[3,4]cyclodeca[1,2-d][1,3]dioxol-8-yl acetate→(3aS,5S,8R,9aS,10S,11aR,13aS,13bR,13cS)-5-Hydroxy-6,9a,14,14-tetramethyl-2,9-dioxo-10-[(triethylsilyl)oxy]-4,5,8,9,9a,10,11,11a,13b,13c-decahydro-2H-3a,7-methano[1,3]dioxolo[9,10]cyclodeca[1,2-d][1]benzoxete-8,13a(13H)-diyl diacetate→Dilithium (3aS,5S,8R,9aS,10S,11aR,13aS,13bR,13cS)-8,13a-bis(acetyloxy)-6,9a,14,14-tetramethyl-9-oxo-2-phenyl-10-[(triethylsilyl)oxy]-4,5,8,9,9a,10,11,11a,13,13a,13b,13c-dodecahydro-2H-3a,7-methano[1,3]dioxolo[9,10]cyclodeca[1,2-d][1]benzoxete-2,5-bis(olate)
(2alpha,5beta,7beta,13alpha)-1-Hydroxy-10-oxo-5,7,13-tris[(triethylsilyl)oxy]taxa-4(20),11-dien-2-yl benzoate→(2alpha,5beta,7beta,13alpha)-1-Hydroxy-9-methyl-10-oxo-5,7,13-tris[(triethylsilyl)oxy]taxa-4(20),11-dien-2-yl benzoate→(2alpha,5alpha,7beta,10beta,13alpha)-10-(Acetyloxy)-5-bromo-1-hydroxy-9-oxo-7,13-bis[(triethylsilyl)oxy]taxa-4(20),11-dien-2-yl benzoate→(2alpha,5beta,7beta,10beta,13alpha)-1,10-Dihydroxy-9-oxo-5,7,13-tris[(triethylsilyl)oxy]taxa-4(20),11-dien-2-yl benzoate→Acetic acid acetic anhydride→(2alpha,5beta,7beta,10beta,13alpha)-10-(Acetyloxy)-1-hydroxy-9-oxo-5,7,13-tris[(triethylsilyl)oxy]taxa-4(20),11-dien-2-yl benzoate→(2alpha,5beta,7beta,10beta,13alpha)-10-(Acetyloxy)-1,5-dihydroxy-9-oxo-7,13-bis[(triethylsilyl)oxy]taxa-4(20),11-dien-2-yl benzoate
(2alpha,5beta,7beta,10beta,13alpha)-4-(Acetyloxy)-1,7,10,13-tetrahydroxy-9-oxo-5,20-epoxytax-11-en-2-yl benzoate→Acetic acid acetic anhydride→(2alpha,5beta,7beta,10beta,13alpha)-4,10-Bis(acetyloxy)-1,7,13-trihydroxy-9-oxo-5,20-epoxytax-11-en-2-yl benzoate→(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-Bis(acetyloxy)-1,15-dihydroxy-10,14,17,17-tetramethyl-11-oxo-9-[(triethylsilyl)oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate→(2alpha,5beta,7beta,10beta,13alpha)-4,10-Bis(acetyloxy)-13-[[(2R,3S)-3-benzamido-2-hydroxy-3-phenylpropanoyl]oxy]-1-hydroxy-9-oxo-7-[(triethylsilyl)oxy]-5,20-epoxytax-11-en-2-yl benzoate→2-Bromanylethanoic acid→(2alpha,5beta,7beta,10beta,13alpha)-4,10-Bis(acetyloxy)-13-[(bromoacetyl)oxy]-1-hydroxy-9-oxo-7-[(triethylsilyl)oxy]-5,20-epoxytax-11-en-2-yl benzoate→(2alpha,5beta,7beta,10beta,13alpha)-4,10-Bis(acetyloxy)-13-[(diazoacetyl)oxy]-1-hydroxy-9-oxo-7-[(triethylsilyl)oxy]-5,20-epoxytax-11-en-2-yl benzoate→N-[(1Z)-Phenylmethylidene]benzamide
(2alpha,5beta,7beta,10beta,13alpha)-4-(Acetyloxy)-1,7,10,13-tetrahydroxy-9-oxo-5,20-epoxytax-11-en-2-yl benzoate→Acetic acid acetic anhydride→(2alpha,5beta,7beta,10beta,13alpha)-4,10-Bis(acetyloxy)-1,7,13-trihydroxy-9-oxo-5,20-epoxytax-11-en-2-yl benzoate→(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-Bis(acetyloxy)-1,15-dihydroxy-10,14,17,17-tetramethyl-11-oxo-9-[(triethylsilyl)oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate→(2alpha,5beta,7beta,10beta,13alpha)-4,10-Bis(acetyloxy)-13-[[(2R,3S)-3-benzamido-2-hydroxy-3-phenylpropanoyl]oxy]-1-hydroxy-9-oxo-7-[(triethylsilyl)oxy]-5,20-epoxytax-11-en-2-yl benzoate→2-Bromanylethanoic acid→(2alpha,5beta,7beta,10beta,13alpha)-4,10-Bis(acetyloxy)-13-[(bromoacetyl)oxy]-1-hydroxy-9-oxo-7-[(triethylsilyl)oxy]-5,20-epoxytax-11-en-2-yl benzoate→(2alpha,5beta,7beta,10beta,13alpha)-4,10-Bis(acetyloxy)-13-[(diazoacetyl)oxy]-1-hydroxy-9-oxo-7-[(triethylsilyl)oxy]-5,20-epoxytax-11-en-2-yl benzoate→N-[(1Z)-Phenylmethylidene]benzamide
Fluticasone Propionate/Formoterol Fumarate HydrateOptimised routesteps: 6total yield: 254.5 mg (FLUT-027)
(Z)-1-((8S,10S,13S,14S)-10,13-dimethyl-3-oxo-7,8,12,13,15,16-hexahydro-3H-cyclopenta[a]phenanthren-17(6H,10H,14H)-ylidene)-2-oxoethyl acetate→2-((8S,10S,13S,14S)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15-octahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate→2-((8S,9R,10S,11S,13S,14S)-9-bromo-11-(formyloxy)-10,13-dimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15-decahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate→2-((4aS,4bS,5aS,6aS,9aS,9bS)-4a,6a-dimethyl-2-oxo-2,4a,5a,6,6a,9,9a,9b,10,11-decahydrocyclopenta[1,2]phenanthro[4,4a-b]oxiren-7-yl)-2-oxoethyl acetate→2-((4aS,4bS,5aS,6aS,7R,8R,9aS,9bS)-7-hydroxy-4a,6a,8-trimethyl-2-oxo-2,4a,5a,6,6a,7,8,9,9a,9b,10,11-dodecahydrocyclopenta[1,2]phenanthro[4,4a-b]oxiren-7-yl)-2-oxoethyl acetate→(8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one→(Z)-2-((8S,10S,13S,14S)-10,13-dimethyl-3-oxo-7,8,12,13,15,16-hexahydro-3H-cyclopenta[a]phenanthren-17(6H,10H,14H)-ylidene)-2-hydroxyacetaldehyde→acetic anhydride
(3,4-Dimethoxypyridin-2-yl)methanol→2-Methylpyridin-3-ol→3-methoxy-2-methylpyridine→3-methoxy-2-methyl-1-oxidopyridin-1-ium→3-methoxy-2-methyl-4-nitro-1-oxido-1-pyridin-1-ylium→3,4-Dimethoxy-2-methylpyridine 1-oxide→Acetic anhydride→(3,4-dimethoxypyridin-2-yl)methyl acetate→3-methoxypyridine→4-Chloro-3-methoxypyridine hydrochloride→2-Oxopropionic acid ethyl ester→ethyl 4-chloro-3-methoxypyridine-2-carboxylate→methyl 3,4-dimethoxypyridine-2-carboxylate
2-Bromo-2',4'-dichloroacetophenone→2',4'-Dichloroacetophenone→Glycerol→[(2S,4R)-2-(bromomethyl)-2-(2,4-dichlorophenyl)-1,3-dioxolan-4-yl]methanol→(±)-cis-2-(Bromomethyl)-2-(2,4-dichlorophenyl)-1,3-dioxolan-4-yl]methyl benzoate→Imidazole→[(2S,4S)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methyl benzoate→[cis-2-(2,4-Dichlorophenyl)-2-[(1H-imidazol-1-yl)methyl]-1,3-dioxolan-4-yl]methanol→[(2S,4S)-2-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methyl methanesulfonate→1-[4-(4-Hydroxyphenyl)piperazin-1-yl]ethanone→4-(Piperazin-1-yl)phenol→Acetic anhydride
(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-Bis(acetyloxy)-1,15-dihydroxy-10,14,17,17-tetramethyl-11-oxo-9-[(triethylsilyl)oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate→(3aS,9aS,10S,11aR,13aS,13bR,13cS)-13a-Hydroxy-6,9a,14,14-tetramethyl-10-[(triethylsilyl)oxy]-4,5,9a,10,11,11a,13,13a,13b,13c-decahydro-3a,7-methano[1,3]dioxolo[9,10]cyclodeca[1,2-d][1]benzoxete-2,8(9H)-dione→Acetic acid acetic anhydride→(2alpha,5beta,7beta,9beta,10beta)-4,10-Diacetoxy-1,9-dihydroxy-7-[(triethylsilyl)oxy]-5,20-epoxytax-11-en-2-yl benzoate→(3aS,9aS,10S,11aR,13aS,13bR,13cS)-6,9a,14,14-Tetramethyl-2,8-dioxo-10-[(triethylsilyl)oxy]-4,5,8,9,9a,10,11,11a,13b,13c-decahydro-3a,7-methano[1,3]dioxolo[9,10]cyclodeca[1,2-d][1]benzoxet-13a(13H)-yl acetate→Lithiumbenzene→(2alpha,5beta,7beta)-4-Acetoxy-1-hydroxy-10-oxo-7-[(triethylsilyl)oxy]-5,20-epoxytax-11-en-2-yl benzoate→(2alpha,5beta,7beta,9beta)-4-Acetoxy-1,9-dihydroxy-10-oxo-7-[(triethylsilyl)oxy]-5,20-epoxytax-11-en-2-yl benzoate
(2alpha,5beta,7beta,10beta,13alpha)-4-(Acetyloxy)-1,7,10,13-tetrahydroxy-9-oxo-5,20-epoxytax-11-en-2-yl benzoate→Acetic acid acetic anhydride→(2alpha,5beta,7beta,10beta,13alpha)-4,10-Bis(acetyloxy)-1,7,13-trihydroxy-9-oxo-5,20-epoxytax-11-en-2-yl benzoate→(2alpha,5beta,7beta,10beta,13alpha)-4,10-Bis(acetyloxy)-1,13-dihydroxy-9-oxo-7-[[(2,2,2-trichloroethoxy)carbonyl]oxy]-5,20-epoxytax-11-en-2-yl benzoate→(3R,4S)-1-Benzoyl-4-phenyl-3-(triethylsiloxy)azetidin-2-one→(2alpha,5beta,7beta,10beta,13alpha)-4,10-Bis(acetyloxy)-1-hydroxy-9-oxo-13-([(2R,3S)-3-phenyl-3-[(phenylcarbonyl)amino]-2-[(triethylsilyl)oxy]propanoyl]oxy)-7-[[(2,2,2-trichloroethoxy)carbonyl]oxy]-5,20-epoxytax-11-en-2-yl benzoate
(2alpha,5beta,7beta,10beta,13alpha)-4-(Acetyloxy)-13-[[(2R,3S)-3-benzamido-2-hydroxy-3-phenylpropanoyl]oxy]-1,7,10-trihydroxy-9-oxo-5,20-epoxytax-11-en-2-yl benzoate→(2alpha,5beta,7beta,10beta,13alpha)-4-(Acetyloxy)-1,10-dihydroxy-9-oxo-13-([(2R,3S)-3-phenyl-3-[(phenylcarbonyl)amino]-2-[(triethylsilyl)oxy]propanoyl]oxy)-7-[(triethylsilyl)oxy]-5,20-epoxytax-11-en-2-yl benzoate→Acetic acid acetic anhydride→(2alpha,5beta,7beta,10beta,13alpha)-4,10-Bis(acetyloxy)-1-hydroxy-9-oxo-13-([(2R,3S)-3-phenyl-3-[(phenylcarbonyl)amino]-2-[(triethylsilyl)oxy]propanoyl]oxy)-7-[(triethylsilyl)oxy]-5,20-epoxytax-11-en-2-yl benzoate
(2alpha,5beta,7beta,10beta,13alpha)-4-(Acetyloxy)-1,7,10,13-tetrahydroxy-9-oxo-5,20-epoxytax-11-en-2-yl benzoate→Acetic acid acetic anhydride→(2alpha,5beta,7beta,10beta,13alpha)-4,10-Bis(acetyloxy)-1,7,13-trihydroxy-9-oxo-5,20-epoxytax-11-en-2-yl benzoate→(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-Bis(acetyloxy)-1,15-dihydroxy-10,14,17,17-tetramethyl-11-oxo-9-[(triethylsilyl)oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate→(2R,4S,5R)-2-(4-Methoxyphenyl)-4-phenyl-3-[(prop-2-en-1-yloxy)carbonyl]-1,3-oxazolidine-5-carboxylic acid→5-[(2alpha,5beta,7beta,10beta,13alpha)-4,10-Bis(acetyloxy)-2-(benzoyloxy)-1-hydroxy-9-oxo-7-[(triethylsilyl)oxy]-5,20-epoxytax-11-en-13-yl] 3-prop-2-en-1-yl (2R,4S,5R)-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-3,5-dicarboxylate→5-[(2alpha,5beta,7beta,10beta,13alpha)-4,10-Bis(acetyloxy)-2-(benzoyloxy)-1,7-dihydroxy-9-oxo-5,20-epoxytax-11-en-13-yl] 3-prop-2-en-1-yl (2R,4S,5R)-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-3,5-dicarboxylate→(2alpha,5beta,7beta,10beta,13alpha)-4,10-Bis(acetyloxy)-2-(benzoyloxy)-1,7-dihydroxy-9-oxo-5,20-epoxytax-11-en-13-yl (2R,4S,5R)-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylate
(1S,5S,10S,11S,12S,16S)-10-(Benzyloxy)-7,11,14,14,18,21,21-heptamethyl-2,4,13,15-tetraoxapentacyclo[15.3.1.0(1,5).0(6,11).0(12,16)]henicosa-6,17-dien-3-one→(3aS,5S,8R,9aS,10S,13bS)-5-Hydroxy-6,9a,13,14,14-pentamethyl-12-[2-(4-methylbenzene-1-sulfonyl)hydrazinylidene]-2,9-dioxo-10-[(triethylsilyl)oxy]-5,8,9,9a,10,11,12,13b-octahydro-2H,4H-3a,7-methanobenzo[3,4]cyclodeca[1,2-d][1,3]dioxol-8-yl acetate→(3aS,5S,8R,9aS,10S,13bS)-6,9a,13,14,14-Pentamethyl-12-[2-(4-methylbenzene-1-sulfonyl)hydrazinylidene]-2,9-dioxo-10-[(triethylsilyl)oxy]-5-[(trimethylsilyl)oxy]-5,8,9,9a,10,11,12,13b-octahydro-2H,4H-3a,7-methanobenzo[3,4]cyclodeca[1,2-d][1,3]dioxol-8-yl acetate→(3aS,8R,9aS,10S,13bS)-10-(Benzyloxy)-6,9a,13,14,14-pentamethyl-2,9-dioxo-5,8,9,9a,10,11,12,13b-octahydro-2H,4H-3a,7-methanobenzo[3,4]cyclodeca[1,2-d][1,3]dioxol-8-yl acetate→(3aS,8R,9aS,10S,13bS)-6,9a,13,14,14-Pentamethyl-2,5,9,12-tetraoxo-10-[(triethylsilyl)oxy]-5,8,9,9a,10,11,12,13b-octahydro-2H,4H-3a,7-methanobenzo[3,4]cyclodeca[1,2-d][1,3]dioxol-8-yl acetate→(3aS,8R,9aS,10S,13bS)-6,9a,13,14,14-Pentamethyl-2,9-dioxo-10-[(triethylsilyl)oxy]-5,8,9,9a,10,11,12,13b-octahydro-2H,4H-3a,7-methanobenzo[3,4]cyclodeca[1,2-d][1,3]dioxol-8-yl acetate→(3aS,8S,9S,9aR,10S,13bS)-10-(Benzyloxy)-8,9-dihydroxy-6,9a,13,14,14-pentamethyl-5,8,9,9a,10,11,12,13b-octahydro-2H,4H-3a,7-methanobenzo[3,4]cyclodeca[1,2-d][1,3]dioxol-2-one→(3aS,8S,9S,9aR,10S,13bS)-10-(Benzyloxy)-9-hydroxy-6,9a,13,14,14-pentamethyl-2-oxo-5,8,9,9a,10,11,12,13b-octahydro-2H,4H-3a,7-methanobenzo[3,4]cyclodeca[1,2-d][1,3]dioxol-8-yl acetate→4-Methylbenzenesulfonhydrazide→Acetic acid acetic anhydride
Acetic acid acetic anhydride→(3aS,5S,8R,9aS,10S,13bS)-6,9a,13,14,14-Pentamethyl-12-[2-(4-methylbenzene-1-sulfonyl)hydrazinylidene]-2,9-dioxo-10-[(triethylsilyl)oxy]-5-[(trimethylsilyl)oxy]-5,8,9,9a,10,11,12,13b-octahydro-2H,4H-3a,7-methanobenzo[3,4]cyclodeca[1,2-d][1,3]dioxol-8-yl acetate→(3aS,5S,8R,9aS,10S,13aR,13bS)-6,9a,13,14,14-Pentamethyl-2,9-dioxo-10-[(triethylsilyl)oxy]-5-[(trimethylsilyl)oxy]-5,8,9,9a,10,11,13a,13b-octahydro-2H,4H-3a,7-methanobenzo[3,4]cyclodeca[1,2-d][1,3]dioxol-8-yl acetate→(3aS,5S,8R,9aS,10S,12S,13aR,13bS)-12-Hydroxy-6,9a,14,14-tetramethyl-13-methylidene-2,9-dioxo-10-[(triethylsilyl)oxy]-5-[(trimethylsilyl)oxy]-5,8,9,9a,10,11,12,13,13a,13b-decahydro-2H,4H-3a,7-methanobenzo[3,4]cyclodeca[1,2-d][1,3]dioxol-8-yl acetate→(3R,4S)-1-Benzoyl-4-phenyl-3-(triethylsiloxy)azetidin-2-one→(3aS,5S,8R,9aS,10S,12S,13aR,13bS)-12-[(Methanesulfonyl)oxy]-6,9a,14,14-tetramethyl-13-methylidene-2,9-dioxo-10-[(triethylsilyl)oxy]-5-[(trimethylsilyl)oxy]-5,8,9,9a,10,11,12,13,13a,13b-decahydro-2H,4H-3a,7-methanobenzo[3,4]cyclodeca[1,2-d][1,3]dioxol-8-yl acetate→(3aS,5S,8R,9aS,10S,12S,13S,13aR,13bS)-13-Hydroxy-13-(hydroxymethyl)-12-[(methanesulfonyl)oxy]-6,9a,14,14-tetramethyl-2,9-dioxo-10-[(triethylsilyl)oxy]-5-[(trimethylsilyl)oxy]-5,8,9,9a,10,11,12,13,13a,13b-decahydro-2H,4H-3a,7-methanobenzo[3,4]cyclodeca[1,2-d][1,3]dioxol-8-yl acetate→(3aS,5S,8R,9aS,10S,11aR,13aS,13bR,13cS)-5-Hydroxy-6,9a,14,14-tetramethyl-2,9-dioxo-10-[(triethylsilyl)oxy]-4,5,8,9,9a,10,11,11a,13b,13c-decahydro-2H-3a,7-methano[1,3]dioxolo[9,10]cyclodeca[1,2-d][1]benzoxete-8,13a(13H)-diyl diacetate→Dilithium (3aS,5S,8R,9aS,10S,11aR,13aS,13bR,13cS)-8,13a-bis(acetyloxy)-6,9a,14,14-tetramethyl-9-oxo-2-phenyl-10-[(triethylsilyl)oxy]-4,5,8,9,9a,10,11,11a,13,13a,13b,13c-dodecahydro-2H-3a,7-methano[1,3]dioxolo[9,10]cyclodeca[1,2-d][1]benzoxete-2,5-bis(olate)
(2alpha,5beta,7beta,13alpha)-1-Hydroxy-10-oxo-5,7,13-tris[(triethylsilyl)oxy]taxa-4(20),11-dien-2-yl benzoate→(2alpha,5beta,7beta,13alpha)-1-Hydroxy-9-methyl-10-oxo-5,7,13-tris[(triethylsilyl)oxy]taxa-4(20),11-dien-2-yl benzoate→(2alpha,5alpha,7beta,10beta,13alpha)-10-(Acetyloxy)-5-bromo-1-hydroxy-9-oxo-7,13-bis[(triethylsilyl)oxy]taxa-4(20),11-dien-2-yl benzoate→(2alpha,5beta,7beta,10beta,13alpha)-1,10-Dihydroxy-9-oxo-5,7,13-tris[(triethylsilyl)oxy]taxa-4(20),11-dien-2-yl benzoate→Acetic acid acetic anhydride→(2alpha,5beta,7beta,10beta,13alpha)-10-(Acetyloxy)-1-hydroxy-9-oxo-5,7,13-tris[(triethylsilyl)oxy]taxa-4(20),11-dien-2-yl benzoate→(2alpha,5beta,7beta,10beta,13alpha)-10-(Acetyloxy)-1,5-dihydroxy-9-oxo-7,13-bis[(triethylsilyl)oxy]taxa-4(20),11-dien-2-yl benzoate
(2alpha,5beta,7beta,10beta,13alpha)-4-(Acetyloxy)-1,7,10,13-tetrahydroxy-9-oxo-5,20-epoxytax-11-en-2-yl benzoate→Acetic acid acetic anhydride→(2alpha,5beta,7beta,10beta,13alpha)-4,10-Bis(acetyloxy)-1,7,13-trihydroxy-9-oxo-5,20-epoxytax-11-en-2-yl benzoate→(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-Bis(acetyloxy)-1,15-dihydroxy-10,14,17,17-tetramethyl-11-oxo-9-[(triethylsilyl)oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate→(2alpha,5beta,7beta,10beta,13alpha)-4,10-Bis(acetyloxy)-13-[[(2R,3S)-3-benzamido-2-hydroxy-3-phenylpropanoyl]oxy]-1-hydroxy-9-oxo-7-[(triethylsilyl)oxy]-5,20-epoxytax-11-en-2-yl benzoate→2-Bromanylethanoic acid→(2alpha,5beta,7beta,10beta,13alpha)-4,10-Bis(acetyloxy)-13-[(bromoacetyl)oxy]-1-hydroxy-9-oxo-7-[(triethylsilyl)oxy]-5,20-epoxytax-11-en-2-yl benzoate→(2alpha,5beta,7beta,10beta,13alpha)-4,10-Bis(acetyloxy)-13-[(diazoacetyl)oxy]-1-hydroxy-9-oxo-7-[(triethylsilyl)oxy]-5,20-epoxytax-11-en-2-yl benzoate→N-[(1Z)-Phenylmethylidene]benzamide
(2alpha,5beta,7beta,10beta,13alpha)-4-(Acetyloxy)-1,7,10,13-tetrahydroxy-9-oxo-5,20-epoxytax-11-en-2-yl benzoate→Acetic acid acetic anhydride→(2alpha,5beta,7beta,10beta,13alpha)-4,10-Bis(acetyloxy)-1,7,13-trihydroxy-9-oxo-5,20-epoxytax-11-en-2-yl benzoate→(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-Bis(acetyloxy)-1,15-dihydroxy-10,14,17,17-tetramethyl-11-oxo-9-[(triethylsilyl)oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate→(2alpha,5beta,7beta,10beta,13alpha)-4,10-Bis(acetyloxy)-13-[[(2R,3S)-3-benzamido-2-hydroxy-3-phenylpropanoyl]oxy]-1-hydroxy-9-oxo-7-[(triethylsilyl)oxy]-5,20-epoxytax-11-en-2-yl benzoate→2-Bromanylethanoic acid→(2alpha,5beta,7beta,10beta,13alpha)-4,10-Bis(acetyloxy)-13-[(bromoacetyl)oxy]-1-hydroxy-9-oxo-7-[(triethylsilyl)oxy]-5,20-epoxytax-11-en-2-yl benzoate→(2alpha,5beta,7beta,10beta,13alpha)-4,10-Bis(acetyloxy)-13-[(diazoacetyl)oxy]-1-hydroxy-9-oxo-7-[(triethylsilyl)oxy]-5,20-epoxytax-11-en-2-yl benzoate→N-[(1Z)-Phenylmethylidene]benzamide
(Z)-1-((8S,10S,13S,14S)-10,13-dimethyl-3-oxo-7,8,12,13,15,16-hexahydro-3H-cyclopenta[a]phenanthren-17(6H,10H,14H)-ylidene)-2-oxoethyl acetate→2-((8S,10S,13S,14S)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15-octahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate→2-((8S,9R,10S,11S,13S,14S)-9-bromo-11-(formyloxy)-10,13-dimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15-decahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate→2-((4aS,4bS,5aS,6aS,9aS,9bS)-4a,6a-dimethyl-2-oxo-2,4a,5a,6,6a,9,9a,9b,10,11-decahydrocyclopenta[1,2]phenanthro[4,4a-b]oxiren-7-yl)-2-oxoethyl acetate→2-((4aS,4bS,5aS,6aS,7R,8R,9aS,9bS)-7-hydroxy-4a,6a,8-trimethyl-2-oxo-2,4a,5a,6,6a,7,8,9,9a,9b,10,11-dodecahydrocyclopenta[1,2]phenanthro[4,4a-b]oxiren-7-yl)-2-oxoethyl acetate→(8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one→(Z)-2-((8S,10S,13S,14S)-10,13-dimethyl-3-oxo-7,8,12,13,15,16-hexahydro-3H-cyclopenta[a]phenanthren-17(6H,10H,14H)-ylidene)-2-hydroxyacetaldehyde→acetic anhydride
2-Bromo-2',4'-dichloroacetophenone→2',4'-Dichloroacetophenone→Glycerol→[(2S,4R)-2-(bromomethyl)-2-(2,4-dichlorophenyl)-1,3-dioxolan-4-yl]methanol→(±)-cis-2-(Bromomethyl)-2-(2,4-dichlorophenyl)-1,3-dioxolan-4-yl]methyl benzoate→Imidazole→[(2S,4S)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methyl benzoate→[cis-2-(2,4-Dichlorophenyl)-2-[(1H-imidazol-1-yl)methyl]-1,3-dioxolan-4-yl]methanol→[(2S,4S)-2-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methyl methanesulfonate→1-[4-(4-Hydroxyphenyl)piperazin-1-yl]ethanone→4-(Piperazin-1-yl)phenol→Acetic anhydride
Resin bound N5-[N-(2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-sulfonyl)carbamimidoyl]-L-ornithyl-S-(triphenylmethyl)-L-cysteinyl-D-alanyl-1-(triphenylmethyl)-L-histidyl-D-phenylalanyl-N5-[N-(2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-sulfonyl)carbamimidoyl]-L-ornithyl-1-(tert-butoxycarbonyl)-L-tryptophyl-S-(triphenylmethyl)-L-cysteinamide→Resin bound N5-[N-(2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-sulfonyl)carbamimidoyl]-L-ornithyl-S-(triphenylmethyl)-L-cysteinyl-D-alanyl-1-(triphenylmethyl)-L-histidyl-D-phenylalanyl-N5-[N-(2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-sulfonyl)carbamimidoyl]-L-ornithyl-L-tryptophyl-S-(triphenylmethyl)-L-cysteinamide→Resin bound N5-[N-(2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-sulfonyl)carbamimidoyl]-L-ornithyl-S-(acetamidomethyl)-L-cysteinyl-D-alanyl-1-(triphenylmethyl)-L-histidyl-D-phenylalanyl-N5-[N-(2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-sulfonyl)carbamimidoyl]-L-ornithyl-L-tryptophyl-S-(acetamidomethyl)-L-cysteinamide→Acetic acid→Acetic acid acetic anhydride→Resin bound N2-acetyl-N5-[N-(2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-sulfonyl)carbamimidoyl]-L-ornithyl-S-(triphenylmethyl)-L-cysteinyl-D-alanyl-1-(triphenylmethyl)-L-histidyl-D-phenylalanyl-N5-[N-(2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-sulfonyl)carbamimidoyl]-L-ornithyl-1-(tert-butoxycarbonyl)-L-tryptophyl-S-(triphenylmethyl)-L-cysteinamide→Resin bound N2-acetyl-N5-[N-(2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-sulfonyl)carbamimidoyl]-L-ornithyl-S-(triphenylmethyl)-L-cysteinyl-D-alanyl-1-(triphenylmethyl)-L-histidyl-D-phenylalanyl-N5-[N-(2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-sulfonyl)carbamimidoyl]-L-ornithyl-L-tryptophyl-S-(triphenylmethyl)-L-cysteinamide→Resin bound [N2-acetyl-N5-[N-(2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-sulfonyl)carbamimidoyl]-L-ornithyl-S-(acetamidomethyl)-L-cysteinyl-D-alanyl-1-(triphenylmethyl)-L-histidyl-D-phenylalanyl-N5-[N-(2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-sulfonyl)carbamimidoyl]-L-ornithyl-L-tryptophyl-S-(acetamidomethyl)-L-cysteinyl]nitrilo
(R)-1-(naphthalen-1-yl)ethan-1-amine→3-(trifluoromethyl)benzaldehyde→acetic anhydride→(E)-3-(3-(trifluoromethyl)phenyl)acrylic acid→3-(3-(trifluoromethyl)phenyl)propanoic acid→(R)-N-(1-(naphthalen-1-yl)ethyl)-3-(3-(trifluoromethyl)phenyl)propanamide
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