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CAS 143527-70-2
(4S,5R)-3-(tert-Butoxycarbonyl)-2,2-dimethyl-4-phenyl-1,3-oxazolidine-5-carboxylic acid
Codes: (IX)101438-10-a, (VI)101438-80-a, (X)140605-2-a, (III)140605-5-a, (III)140605-12-a, (VI)140605-27-a
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）
Source drugs (routes using this intermediate)
| Drug | Tier | Expiry |
|---|---|---|
| Paclitaxel/Encequidar mesylate | Tier C — Watch / trade | - |
| Docetaxel polymeric micelle (Samyang Biopharmaceuticals) | Tier C — Watch / trade | - |
| Paclitaxel | Tier B — Position early | - |
| Docetaxel （Beihai） | Tier 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.
(4S,5R)-3-(2-bromoacetyl)-4-methyl-5-phenyl-1,3-oxazolidin-2-one→Benzaldehyde→(4S,5R)-3-[(2S,3R)-2-bromo-3-hydroxy-3-phenylpropanoyl]-4-methyl-5-phenyl-1,3-oxazolidin-2-one→Ethyl (2R,3R)-3-phenyloxirane-2-carboxylate→(4S,5R)-3-(tert-Butoxycarbonyl)-2,2-dimethyl-4-phenyl-1,3-oxazolidine-5-carboxylic acid→Ethyl (2R,3S)-3-azido-2-hydroxy-3-phenylpropanoate→Ethyl (2R,3S)-3-amino-2-hydroxy-3-phenylpropanoate→Ethyl (2R,3S)-3-[(tert-butoxycarbonyl)amino]-2-hydroxy-3-phenylpropanoate→3-tert-butyl 5-ethyl (4S,5R)-2,2-dimethyl-4-phenyl-1,3-oxazolidine-3,5-dicarboxylate→(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→5-(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetyloxy)-2-(benzoyloxy)-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-9-{[(2,2,2-trichloroethoxy)carbonyl]oxy}-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-15-yl 3-tert-butyl (4S,5R)-2,2-dimethyl-4-phenyl-1,3-oxazolidine-3,5-dicarboxylate→(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetyloxy)-15-{[(2R,3S)-3-amino-2-hydroxy-3-phenylpropanoyl]oxy}-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-9-{[(2,2,2-trichloroethoxy)carbonyl]oxy}-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)-1-hydroxy-15-{[(2R,3S)-2-hydroxy-3-phenyl-3-(phenylformamido)propanoyl]oxy}-10,14,17,17-tetramethyl-11-oxo-9-{[(2,2,2-trichloroethoxy)carbonyl]oxy}-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate
13-Acetyl-9-dihydrobaccatin-III→(2alpha,5beta,7beta,9alpha,10beta,13alpha)-4,13-Bis(acetyloxy)-1,7,9,10-tetrahydroxy-5,20-epoxytax-11-en-2-yl benzoate→(2alpha,5beta,7beta,9alpha,10beta,13alpha)-4,13-Bis(acetyloxy)-7-[[tert-butyl(diphenyl)silyl]oxy]-1,9,10-trihydroxy-5,20-epoxytax-11-en-2-yl benzoate→(2alpha,5beta,7beta,9alpha,13alpha)-4,13-Bis(acetyloxy)-7-[[tert-butyl(diphenyl)silyl]oxy]-1,9-dihydroxy-10-oxo-5,20-epoxytax-11-en-2-yl benzoate→(2alpha,5beta,7beta,9alpha,13alpha)-4-(Acetyloxy)-7-[[tert-butyl(diphenyl)silyl]oxy]-1,9,13-trihydroxy-10-oxo-5,20-epoxytax-11-en-2-yl benzoate→(4S,5R)-3-(tert-Butoxycarbonyl)-2,2-dimethyl-4-phenyl-1,3-oxazolidine-5-carboxylic acid→5-[(2alpha,5beta,7beta,9alpha,13alpha)-4-(Acetyloxy)-2-(benzoyloxy)-7-[[tert-butyl(diphenyl)silyl]oxy]-1,9-dihydroxy-10-oxo-5,20-epoxytax-11-en-13-yl] 3-tert-butyl (4S)-2,2-dimethyl-4-phenyl-1,3-oxazolidine-3,5-dicarboxylate→(2alpha,5beta,7beta,9alpha,13alpha)-4-(Acetyloxy)-13-([(2R,3S)-3-[(tert-butoxycarbonyl)amino]-2-hydroxy-3-phenylpropanoyl]oxy)-1,7,9-trihydroxy-10-oxo-5,20-epoxytax-11-en-2-yl benzoate
(S)-(+)-2-Phenylglycine→Methyl trifluoromethanesulfonate→Bis(1,1-dimethylethyl) dicarbonoate→(S)-N-Boc-phenylglycine methyl ester→N-(tert-Butoxycarbonyl)-L-2-phenylglycinal→2-(trimethylsilyl)-1,3-thiazole→tert-butyl N-[(1S,2R)-2-hydroxy-1-phenyl-2-(1,3-thiazol-2-yl)ethyl]carbamate→1-Methoxy-1-methylethyl methyl ether→tert-butyl (4S,5R)-2,2-dimethyl-4-phenyl-5-(1,3-thiazol-2-yl)-1,3-oxazolidine-3-carboxylate→tert-butyl (4S,5R)-5-formyl-2,2-dimethyl-4-phenyl-1,3-oxazolidine-3-carboxylate→(4S,5R)-3-(tert-Butoxycarbonyl)-2,2-dimethyl-4-phenyl-1,3-oxazolidine-5-carboxylic acid
(2alpha,5beta,7beta,10beta,13alpha)-4-(Acetyloxy)-1,7,10,13-tetrahydroxy-9-oxo-5,20-epoxytax-11-en-2-yl benzoate→(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetyloxy)-2-(benzoyloxy)-1,15-dihydroxy-9-(1H-imidazol-1-ylcarbonyloxy)-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-12-yl 1H-imidazole-1-carboxylate→(4S,5R)-3-(tert-Butoxycarbonyl)-2,2-dimethyl-4-phenyl-1,3-oxazolidine-5-carboxylic acid→5-(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetyloxy)-2-(benzoyloxy)-1-hydroxy-9,12-bis(imidazol-1-ylcarbonyloxy)-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-15-yl 3-tert-butyl (4S,5R)-2,2-dimethyl-4-phenyl-1,3-oxazolidine-3,5-dicarboxylate→(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(Acetyloxy)-15-[[(2R,3S)-3-amino-2-hydroxy-3-phenylpropanoyl]oxy]-1,9,12-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
(2alpha,5beta,7beta,10beta,13alpha)-4-(Acetyloxy)-1,7,10,13-tetrahydroxy-9-oxo-5,20-epoxytax-11-en-2-yl benzoate→(2alpha,5beta,7beta,10beta,13alpha)-4-Acetoxy-1,13-dihydroxy-9-oxo-7,10-bis[[(2,2,2-trichloroethoxy)carbonyl]oxy]-5,20-epoxytax-11-en-2-yl benzoate→(4S,5R)-3-(tert-Butoxycarbonyl)-2,2-dimethyl-4-phenyl-1,3-oxazolidine-5-carboxylic acid→5-[(2alpha,5beta,7beta,10beta,13alpha)-4-Acetoxy-2-(benzoyloxy)-1-hydroxy-9-oxo-7,10-bis[[(2,2,2-trichloroethoxy)carbonyl]oxy]-5,20-epoxytax-11-en-13-yl] 3-tert-butyl (4S,5R)-2,2-dimethyl-4-phenyl-1,3-oxazolidine-3,5-dicarboxylate→5-[(2alpha,5beta,7beta,10beta,13alpha)-4-Acetoxy-2-(benzoyloxy)-1,7,10-trihydroxy-9-oxo-5,20-epoxytax-11-en-13-yl] 3-tert-butyl (4S,5R)-2,2-dimethyl-4-phenyl-1,3-oxazolidine-3,5-dicarboxylate→(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(Acetyloxy)-15-[[(2R,3S)-3-amino-2-hydroxy-3-phenylpropanoyl]oxy]-1,9,12-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
Isopropyl (2E)-3-phenylacrylate→1,1-Dimethylethyl carbamate→Isopropyl (2R,3S)-3-[(tert-butoxycarbonyl)amino]-2-hydroxy-3-phenylpropanoate→2-Methoxy-1-propene→3-tert-Butyl 5-isopropyl (4S,5R)-2,2-dimethyl-4-phenyl-1,3-oxazolidine-3,5-dicarboxylate→(4S,5R)-3-(tert-Butoxycarbonyl)-2,2-dimethyl-4-phenyl-1,3-oxazolidine-5-carboxylic acid
(4S,5R)-3-(2-bromoacetyl)-4-methyl-5-phenyl-1,3-oxazolidin-2-one→Benzaldehyde→(4S,5R)-3-[(2S,3R)-2-bromo-3-hydroxy-3-phenylpropanoyl]-4-methyl-5-phenyl-1,3-oxazolidin-2-one→Ethyl (2R,3R)-3-phenyloxirane-2-carboxylate→(4S,5R)-3-(tert-Butoxycarbonyl)-2,2-dimethyl-4-phenyl-1,3-oxazolidine-5-carboxylic acid→Ethyl (2R,3S)-3-azido-2-hydroxy-3-phenylpropanoate→Ethyl (2R,3S)-3-amino-2-hydroxy-3-phenylpropanoate→Ethyl (2R,3S)-3-[(tert-butoxycarbonyl)amino]-2-hydroxy-3-phenylpropanoate→3-tert-butyl 5-ethyl (4S,5R)-2,2-dimethyl-4-phenyl-1,3-oxazolidine-3,5-dicarboxylate→(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→5-(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetyloxy)-2-(benzoyloxy)-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-9-{[(2,2,2-trichloroethoxy)carbonyl]oxy}-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-15-yl 3-tert-butyl (4S,5R)-2,2-dimethyl-4-phenyl-1,3-oxazolidine-3,5-dicarboxylate→(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetyloxy)-15-{[(2R,3S)-3-amino-2-hydroxy-3-phenylpropanoyl]oxy}-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-9-{[(2,2,2-trichloroethoxy)carbonyl]oxy}-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)-1-hydroxy-15-{[(2R,3S)-2-hydroxy-3-phenyl-3-(phenylformamido)propanoyl]oxy}-10,14,17,17-tetramethyl-11-oxo-9-{[(2,2,2-trichloroethoxy)carbonyl]oxy}-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate
13-Acetyl-9-dihydrobaccatin-III→(2alpha,5beta,7beta,9alpha,10beta,13alpha)-4,13-Bis(acetyloxy)-1,7,9,10-tetrahydroxy-5,20-epoxytax-11-en-2-yl benzoate→(2alpha,5beta,7beta,9alpha,10beta,13alpha)-4,13-Bis(acetyloxy)-7-[[tert-butyl(diphenyl)silyl]oxy]-1,9,10-trihydroxy-5,20-epoxytax-11-en-2-yl benzoate→(2alpha,5beta,7beta,9alpha,13alpha)-4,13-Bis(acetyloxy)-7-[[tert-butyl(diphenyl)silyl]oxy]-1,9-dihydroxy-10-oxo-5,20-epoxytax-11-en-2-yl benzoate→(2alpha,5beta,7beta,9alpha,13alpha)-4-(Acetyloxy)-7-[[tert-butyl(diphenyl)silyl]oxy]-1,9,13-trihydroxy-10-oxo-5,20-epoxytax-11-en-2-yl benzoate→(4S,5R)-3-(tert-Butoxycarbonyl)-2,2-dimethyl-4-phenyl-1,3-oxazolidine-5-carboxylic acid→5-[(2alpha,5beta,7beta,9alpha,13alpha)-4-(Acetyloxy)-2-(benzoyloxy)-7-[[tert-butyl(diphenyl)silyl]oxy]-1,9-dihydroxy-10-oxo-5,20-epoxytax-11-en-13-yl] 3-tert-butyl (4S)-2,2-dimethyl-4-phenyl-1,3-oxazolidine-3,5-dicarboxylate→(2alpha,5beta,7beta,9alpha,13alpha)-4-(Acetyloxy)-13-([(2R,3S)-3-[(tert-butoxycarbonyl)amino]-2-hydroxy-3-phenylpropanoyl]oxy)-1,7,9-trihydroxy-10-oxo-5,20-epoxytax-11-en-2-yl benzoate
(S)-(+)-2-Phenylglycine→1,1,1,-Trifluoromethanesulfonic acid methyl ester→Bis(1,1-dimethylethyl) dicarbonoate→(S)-N-Boc-phenylglycine methyl ester→N-(tert-Butoxycarbonyl)-L-2-phenylglycinal→2-(trimethylsilyl)-1,3-thiazole→tert-butyl N-[(1S,2R)-2-hydroxy-1-phenyl-2-(1,3-thiazol-2-yl)ethyl]carbamate→1-Methoxy-1-methylethyl methyl ether→tert-butyl (4S,5R)-2,2-dimethyl-4-phenyl-5-(1,3-thiazol-2-yl)-1,3-oxazolidine-3-carboxylate→tert-butyl (4S,5R)-5-formyl-2,2-dimethyl-4-phenyl-1,3-oxazolidine-3-carboxylate→(4S,5R)-3-(tert-Butoxycarbonyl)-2,2-dimethyl-4-phenyl-1,3-oxazolidine-5-carboxylic acid
(2alpha,5beta,7beta,10beta,13alpha)-4-(Acetyloxy)-1,7,10,13-tetrahydroxy-9-oxo-5,20-epoxytax-11-en-2-yl benzoate→(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetyloxy)-2-(benzoyloxy)-1,15-dihydroxy-9-(1H-imidazol-1-ylcarbonyloxy)-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-12-yl 1H-imidazole-1-carboxylate→(4S,5R)-3-(tert-Butoxycarbonyl)-2,2-dimethyl-4-phenyl-1,3-oxazolidine-5-carboxylic acid→5-(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetyloxy)-2-(benzoyloxy)-1-hydroxy-9,12-bis(imidazol-1-ylcarbonyloxy)-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-15-yl 3-tert-butyl (4S,5R)-2,2-dimethyl-4-phenyl-1,3-oxazolidine-3,5-dicarboxylate→(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(Acetyloxy)-15-[[(2R,3S)-3-amino-2-hydroxy-3-phenylpropanoyl]oxy]-1,9,12-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
(2alpha,5beta,7beta,10beta,13alpha)-4-(Acetyloxy)-1,7,10,13-tetrahydroxy-9-oxo-5,20-epoxytax-11-en-2-yl benzoate→(2alpha,5beta,7beta,10beta,13alpha)-4-Acetoxy-1,13-dihydroxy-9-oxo-7,10-bis[[(2,2,2-trichloroethoxy)carbonyl]oxy]-5,20-epoxytax-11-en-2-yl benzoate→(4S,5R)-3-(tert-Butoxycarbonyl)-2,2-dimethyl-4-phenyl-1,3-oxazolidine-5-carboxylic acid→5-[(2alpha,5beta,7beta,10beta,13alpha)-4-Acetoxy-2-(benzoyloxy)-1-hydroxy-9-oxo-7,10-bis[[(2,2,2-trichloroethoxy)carbonyl]oxy]-5,20-epoxytax-11-en-13-yl] 3-tert-butyl (4S,5R)-2,2-dimethyl-4-phenyl-1,3-oxazolidine-3,5-dicarboxylate→5-[(2alpha,5beta,7beta,10beta,13alpha)-4-Acetoxy-2-(benzoyloxy)-1,7,10-trihydroxy-9-oxo-5,20-epoxytax-11-en-13-yl] 3-tert-butyl (4S,5R)-2,2-dimethyl-4-phenyl-1,3-oxazolidine-3,5-dicarboxylate→(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(Acetyloxy)-15-[[(2R,3S)-3-amino-2-hydroxy-3-phenylpropanoyl]oxy]-1,9,12-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
Isopropyl (2E)-3-phenylacrylate→1,1-Dimethylethyl carbamate→Isopropyl (2R,3S)-3-[(tert-butoxycarbonyl)amino]-2-hydroxy-3-phenylpropanoate→2-Methoxy-1-propene→3-tert-Butyl 5-isopropyl (4S,5R)-2,2-dimethyl-4-phenyl-1,3-oxazolidine-3,5-dicarboxylate→(4S,5R)-3-(tert-Butoxycarbonyl)-2,2-dimethyl-4-phenyl-1,3-oxazolidine-5-carboxylic acid
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