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CAS 32981-86-5

(2alpha,5beta,7beta,10beta,13alpha)-4-(Acetyloxy)-1,7,10,13-tetrahydroxy-9-oxo-5,20-epoxytax-11-en-2-yl benzoate(2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-12b-acetoxy-4,6,9,11-tetrahydroxy-4a,8,13,13-tetramethyl-5-oxo-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxet-12-yl benzoate

Codes: (XIII)101438-2-a, (I)101438-8-a, (XI)101438-21-a, (I)101438-33-a, (I)101438-43-a, (VI)101438-47-a, (I)101438-52-a, (I)101438-58-a, (I)101438-77-a, (I)140605-5-a, (I)140605-6-a, (I)140605-12-a +9 more

Application context (from source-drug indications)

Breast cancerPaclitaxel/Encequidar mesylateAdenocarcinomaPaclitaxel/Encequidar mesylateAngiosarcomaPaclitaxel/Encequidar mesylateSolid tumourPaclitaxel/Encequidar mesylateBladder cancerDocetaxel polymeric micelle (Samyang Biopharmaceuticals)Head and neck cancerDocetaxel polymeric micelle (Samyang Biopharmaceuticals)Head and neck squamous cell carcinomaDocetaxel polymeric micelle (Samyang Biopharmaceuticals)Solid tumourDocetaxel polymeric micelle (Samyang Biopharmaceuticals)Pancreatic cancerPaclitaxelNon-small cell lung cancerPaclitaxelHodgkin's diseasePaclitaxelSeminomaPaclitaxelOvarian cancerPaclitaxelBreast cancerPaclitaxelNon-small cell lung cancerDocetaxel (Beihai)Prostate cancerDocetaxel (Beihai)Castration-resistant prostate cancerDocetaxel (Beihai)Breast cancerDocetaxel (Beihai)Head and neck cancerDocetaxel (Beihai)Head and neck squamous cell carcinomaDocetaxel (Beihai)Prostate cancerCabazitaxelAdenocarcinomaCabazitaxel食管胃结合部肿瘤CabazitaxelGastric cancerCabazitaxel生殖细胞和胚胎肿瘤Cabazitaxel睾丸肿瘤Cabazitaxel

Source drugs (routes using this intermediate)

DrugTierExpiry
Paclitaxel/Encequidar mesylateTier C — Watch / trade-
Docetaxel polymeric micelle (Samyang Biopharmaceuticals)Tier C — Watch / trade-
PaclitaxelTier B — Position early-
Docetaxel (Beihai)Tier C — Watch / trade-
CabazitaxelTier C — Watch / trade-

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.

Paclitaxel/Encequidar mesylateOptimised routesteps: 9total yield: /
Paclitaxel/Encequidar mesylateOptimised routesteps: 4total yield: /
(2alpha,5beta,7beta,10beta,13alpha)-4-(Acetyloxy)-1,7,10,13-tetrahydroxy-9-oxo-5,20-epoxytax-11-en-2-yl benzoate→dichlorodiethylsilane→(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetyloxy)-9-{[diethyl(methoxy)silyl]oxy}-1,12,15-trihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate→(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetyloxy)-9-{[diethyl(methoxy)silyl]oxy}-1,15-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate→(4S,5R)-2,4-Diphenyl-4,5-dihydro-1,3-oxazole-5-carboxylic acid→(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetyloxy)-2-(benzoyloxy)-9-{[diethyl(methoxy)silyl]oxy}-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-15-yl (4S,5R)-2,4-diphenyl-4,5-dihydro-1,3-oxazole-5-carboxylate
Paclitaxel/Encequidar mesylateOptimised routesteps: 5total yield: /
Paclitaxel/Encequidar mesylateOptimised routesteps: 5total yield: /
(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
Paclitaxel/Encequidar mesylateOptimised routesteps: 1total yield: /
(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
Docetaxel polymeric micelle (Samyang Biopharmaceuticals)Optimised routesteps: 1total yield: /
(2alpha,5beta,7beta,10beta,13alpha)-4-(Acetyloxy)-1,7,10,13-tetrahydroxy-9-oxo-5,20-epoxytax-11-en-2-yl benzoate→(2R,3S)-3-[(tert-Butoxycarbonyl)amino]-2-hydroxy-3-phenylpropanoic acid
Docetaxel polymeric micelle (Samyang Biopharmaceuticals)Optimised routesteps: 1total yield: /
PaclitaxelOptimised routesteps: 9total yield: /
PaclitaxelOptimised routesteps: 4total yield: /
(2alpha,5beta,7beta,10beta,13alpha)-4-(Acetyloxy)-1,7,10,13-tetrahydroxy-9-oxo-5,20-epoxytax-11-en-2-yl benzoate→dichlorodiethylsilane→(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetyloxy)-9-{[diethyl(methoxy)silyl]oxy}-1,12,15-trihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate→(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetyloxy)-9-{[diethyl(methoxy)silyl]oxy}-1,15-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate→(4S,5R)-2,4-Diphenyl-4,5-dihydro-1,3-oxazole-5-carboxylic acid→(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetyloxy)-2-(benzoyloxy)-9-{[diethyl(methoxy)silyl]oxy}-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-15-yl (4S,5R)-2,4-diphenyl-4,5-dihydro-1,3-oxazole-5-carboxylate
PaclitaxelOptimised routesteps: 5total yield: /
PaclitaxelOptimised routesteps: 5total yield: /
(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
PaclitaxelOptimised routesteps: 1total yield: /
(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
Docetaxel (Beihai)Optimised routesteps: 1total yield: /
(2alpha,5beta,7beta,10beta,13alpha)-4-(Acetyloxy)-1,7,10,13-tetrahydroxy-9-oxo-5,20-epoxytax-11-en-2-yl benzoate→(2R,3S)-3-[(tert-Butoxycarbonyl)amino]-2-hydroxy-3-phenylpropanoic acid
Docetaxel (Beihai)Optimised routesteps: 1total yield: /
CabazitaxelOptimised routesteps: 7total yield: 5.18 g
(2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-12b-acetoxy-4,6,9,11-tetrahydroxy-4a,8,13,13-tetramethyl-5-oxo-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxet-12-yl benzoate→(2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-12b-acetoxy-9,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-4,6-bis(((2,2,2-trichloroethoxy)carbonyl)oxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxet-12-yl benzoate→((chloromethoxy)methyl)benzene→(2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-12b-acetoxy-9-((benzyloxy)methoxy)-11-hydroxy-4a,8,13,13-tetramethyl-5-oxo-4,6-bis(((2,2,2-trichloroethoxy)carbonyl)oxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxet-12-yl benzoate→(2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-12b-acetoxy-9-((benzyloxy)methoxy)-4,6,11-trihydroxy-4a,8,13,13-tetramethyl-5-oxo-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxet-12-yl benzoate→(2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-12b-acetoxy-9-((benzyloxy)methoxy)-11-hydroxy-4,6-dimethoxy-4a,8,13,13-tetramethyl-5-oxo-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxet-12-yl benzoate→(2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-12b-acetoxy-9,11-dihydroxy-4,6-dimethoxy-4a,8,13,13-tetramethyl-5-oxo-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxet-12-yl benzoate→(4S,5R)-3-(tert-butoxycarbonyl)-2-(4-methoxyphenyl)-4-phenyloxazolidine-5-carboxylic acid→5-((2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-12b-acetoxy-12-(benzoyloxy)-4,11-dihydroxy-6-methoxy-4a,8,13,13-tetramethyl-5-oxo-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxet-9-yl) 3-(tert-butyl) (4S,5R)-2-(4-methoxyphenyl)-4-phenyloxazolidine-3,5-dicarboxylate

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