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CAS 24424-99-5
Bis(1,1-dimethylethyl) dicarbonoateDi(tert-butyl)dicarbonate
Codes: 140605-2-a, (VI)140605-15-a, (XI)140605-17-a, (VIII)140605-22-a, (X)140605-24-a, (VI)140605-26-a, Cefcamate Pivoxil Hydrochloride-032
Application context (from source-drug indications)
Bladder 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)Non-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）Bacterial infectionCefcamate Pivoxil Hydrochloride
Source drugs (routes using this intermediate)
| Drug | Tier | Expiry |
|---|---|---|
| Docetaxel polymeric micelle (Samyang Biopharmaceuticals) | Tier C — Watch / trade | - |
| Docetaxel （Beihai） | Tier C — Watch / trade | - |
| Cefcamate Pivoxil Hydrochloride | 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.
(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
(S)-(+)-2-Phenylglycine→tert-Butyl [(1S)-2-hydroxy-1-phenylethyl]carbamate→tert-Butyl [(1S)-2-cyano-2-hydroxy-1-phenylethyl]carbamate→Methyl (3S)-3-amino-2-hydroxy-3-phenylpropanoate hydrogen chloride (1/1)→Phosgene→Bis(1,1-dimethylethyl) dicarbonoate→3-tert-Butyl 5-methyl (4S,5R)-2-oxo-4-phenyl-1,3-oxazolidine-3,5-dicarboxylate→3(S)-(tert-Butoxycarbonylamino)-2(R)-hydroxy-3-phenylpropionic acid methyl ester→1-(Dimethoxymethyl)-4-methoxybenzene→(X)140605-15-a→(2R,4S,5R)-3-(tert-Butoxycarbonyl)-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid
(2R,3S)-3-Amino-2-hydroxy-3-phenylpropanoic acid methyl ester hydrochloride→(2R,3S)-2-Hydroxy-3-phenyl-3-[[(prop-2-en-1-yloxy)carbonyl]amino]propanoic acid methyl ester→1-(Dimethoxymethyl)-4-methoxybenzene→(2R,4S,5R)-2-(4-Methoxyphenyl)-4-phenyl-1,3-oxazolidine-3,5-dicarboxylic acid 5-methyl 3-prop-2-en-1-yl ester→(2R,4S,5R)-2-(4-Methoxyphenyl)-4-phenyl-3-[(prop-2-en-1-yloxy)carbonyl]-1,3-oxazolidine-5-carboxylic acid→(VI)140605-17-a→(2alpha,5beta,7beta,10beta,13alpha)-4-(Acetyloxy)-1,7,10,13-tetrahydroxy-9-oxo-5,20-epoxytax-11-en-2-yl benzoate→(VIII)140605-17-a→(IX)140605-17-a→(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→Bis(1,1-dimethylethyl) dicarbonoate
Benzaldehyde→1-Hydroxyacetone→(3R,4S)-3-Hydroxy-4-[(4-methoxyphenyl)amino]-4-phenylbutan-2-one→(4S,5R)-5-Acetyl-3-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidin-2-one→(4S,5R)-5-Acetyl-4-phenyl-1,3-oxazolidin-2-one→(2R,3S)-3-Amino-2-hydroxy-3-phenylpropanoic acid→(2R,3S)-3-Phenylisoserine methyl ester→Bis(1,1-dimethylethyl) dicarbonoate→3(S)-(tert-Butoxycarbonylamino)-2(R)-hydroxy-3-phenylpropionic acid methyl ester→4-(Methyloxy)benzaldehyde→2-(4-Methoxyphenyl)-4(S)-phenyloxazolidine-3,5(R)-dicarboxylic acid 3-tert-butyl 5-methyl diester→(4S,5R)-3-(tert-Butoxycarbonyl)-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid→Benzoic acid (2alpha,5beta,7beta,9beta,10beta,13alpha)-4,10-diacetoxy-1,9,13-trihydroxy-7-[methyl(diphenyl)silyloxy]-5,20-epoxytax-11-en-2-yl ester→2-(4-Methoxyphenyl)-4(S)-phenyloxazolidine-3,5(R)-dicarboxylic acid 3-tert-butyl 5-[(2aR,4S,4aR,5S,6R,9S,11S,12S,12aR,12bS)-6,12b-diacetoxy-12-(benzoyloxy)-5,11-dihydroxy-4a,8,13,13-tetramethyl-4-[methyl(diphenyl)silyloxy]-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] diester
Benzaldehyde→1-Amino-4-methoxybenzene→2-Hydroxy-1-phenylethanone→2-Hydroxyacetic acid methyl ester→(2R,3S)-2-Hydroxy-3-[(4-methoxyphenyl)amino]-1,3-diphenylpropan-1-one→Methyl (2R,3S)-2-hydroxy-3-[(4-methoxyphenyl)amino]-3-phenylpropanoate→(2R,3S)-3-Phenylisoserine methyl ester→(2R,3S)-3-Amino-2-hydroxy-3-phenylpropanoic acid methyl ester hydrochloride→(4S,5R)-3-(4-Methoxyphenyl)-4-phenyl-5-(phenylcarbonyl)-1,3-oxazolidin-2-one→Methyl (4S,5R)-3-(4-methoxyphenyl)-2-oxo-4-phenyl-1,3-oxazolidine-5-carboxylate→(4S,5R)-4-Phenyl-5-(phenylcarbonyl)-1,3-oxazolidin-2-one→Methyl (4S,5R)-2-oxo-4-phenyl-1,3-oxazolidine-5-carboxylate→Phenyl (4S,5R)-2-oxo-4-phenyl-1,3-oxazolidine-5-carboxylate→(2R,3S)-3-Amino-2-hydroxy-3-phenylpropanoic acid→Bis(1,1-dimethylethyl) dicarbonoate→3(S)-(tert-Butoxycarbonylamino)-2(R)-hydroxy-3-phenylpropionic acid methyl ester→Methyl (2R,3S)-2-hydroxy-3-phenyl-3-[[(1S)-1-phenylethyl]amino]propanoate
(2alpha,5beta,7beta,10beta,13alpha)-4-(Acetyloxy)-1,7,10,13-tetrahydroxy-9-oxo-5,20-epoxytax-11-en-2-yl benzoate→Benzoic acid (3R,7R,12R)-4(S)-(acetyloxy)-1(S),15(S)-dihydroxy-10(S),14,17,17-tetramethyl-11-oxo-9(S),12(R)-bis[(2(S)2,2,2-trichloroacetyl)oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl ester→(4S,5R)-4-Phenyl-2-(tribromomethyl)-1,3-oxazolidine-5-carboxylic acid→(2alpha,5beta,7beta,10beta,13alpha)-4-(Acetyloxy)-1-hydroxy-9-oxo-2-[(phenylcarbonyl)oxy]-7,10-bis[(trichloroacetyl)oxy]-5,20-epoxytax-11-en-13-yl (4S,5R)-4-phenyl-2-(tribromomethyl)-1,3-oxazolidine-5-carboxylate→(2alpha,5beta,7beta,10beta,13alpha)-4-(Acetyloxy)-13-[[(2R,3S)-3-amino-2-hydroxy-3-phenylpropanoyl]oxy]-1-hydroxy-9-oxo-7,10-bis[(trichloroacetyl)oxy]-5,20-epoxytax-11-en-2-yl benzoate→Bis(1,1-dimethylethyl) dicarbonoate→(2alpha,5beta,7beta,10beta,13alpha)-4-(Acetyloxy)-13-([(2R,3S)-3-[(tert-butoxycarbonyl)amino]-2-hydroxy-3-phenylpropanoyl]oxy)-1-hydroxy-9-oxo-7,10-bis[(trichloroacetyl)oxy]-5,20-epoxytax-11-en-2-yl benzoate→(2R,3S)-3-Phenylisoserine methyl ester→Tribromoacetaldehyde→Methyl (4S,5R)-4-phenyl-2-(tribromomethyl)-1,3-oxazolidine-5-carboxylate
(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
(S)-(+)-2-Phenylglycine→tert-Butyl [(1S)-2-hydroxy-1-phenylethyl]carbamate→tert-Butyl [(1S)-2-cyano-2-hydroxy-1-phenylethyl]carbamate→Methyl (3S)-3-amino-2-hydroxy-3-phenylpropanoate hydrogen chloride (1/1)→Carbon oxychloride→Bis(1,1-dimethylethyl) dicarbonoate→3-tert-Butyl 5-methyl (4S,5R)-2-oxo-4-phenyl-1,3-oxazolidine-3,5-dicarboxylate→3(S)-(tert-Butoxycarbonylamino)-2(R)-hydroxy-3-phenylpropionic acid methyl ester→1-(Dimethoxymethyl)-4-methoxybenzene→(X)140605-15-a→(2R,4S,5R)-3-(tert-Butoxycarbonyl)-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid
(2R,3S)-3-Amino-2-hydroxy-3-phenylpropanoic acid methyl ester hydrochloride→(2R,3S)-2-Hydroxy-3-phenyl-3-[[(prop-2-en-1-yloxy)carbonyl]amino]propanoic acid methyl ester→1-(Dimethoxymethyl)-4-methoxybenzene→(2R,4S,5R)-2-(4-Methoxyphenyl)-4-phenyl-1,3-oxazolidine-3,5-dicarboxylic acid 5-methyl 3-prop-2-en-1-yl ester→(2R,4S,5R)-2-(4-Methoxyphenyl)-4-phenyl-3-[(prop-2-en-1-yloxy)carbonyl]-1,3-oxazolidine-5-carboxylic acid→(VI)140605-17-a→(2alpha,5beta,7beta,10beta,13alpha)-4-(Acetyloxy)-1,7,10,13-tetrahydroxy-9-oxo-5,20-epoxytax-11-en-2-yl benzoate→(VIII)140605-17-a→(IX)140605-17-a→(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→Bis(1,1-dimethylethyl) dicarbonoate
Benzaldehyde→1-Hydroxyacetone→(3R,4S)-3-Hydroxy-4-[(4-methoxyphenyl)amino]-4-phenylbutan-2-one→(4S,5R)-5-Acetyl-3-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidin-2-one→(4S,5R)-5-Acetyl-4-phenyl-1,3-oxazolidin-2-one→(2R,3S)-3-Amino-2-hydroxy-3-phenylpropanoic acid→(2R,3S)-3-Phenylisoserine methyl ester→Bis(1,1-dimethylethyl) dicarbonoate→3(S)-(tert-Butoxycarbonylamino)-2(R)-hydroxy-3-phenylpropionic acid methyl ester→4-(Methyloxy)benzaldehyde→2-(4-Methoxyphenyl)-4(S)-phenyloxazolidine-3,5(R)-dicarboxylic acid 3-tert-butyl 5-methyl diester→(4S,5R)-3-(tert-Butoxycarbonyl)-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid→Benzoic acid (2alpha,5beta,7beta,9beta,10beta,13alpha)-4,10-diacetoxy-1,9,13-trihydroxy-7-[methyl(diphenyl)silyloxy]-5,20-epoxytax-11-en-2-yl ester→2-(4-Methoxyphenyl)-4(S)-phenyloxazolidine-3,5(R)-dicarboxylic acid 3-tert-butyl 5-[(2aR,4S,4aR,5S,6R,9S,11S,12S,12aR,12bS)-6,12b-diacetoxy-12-(benzoyloxy)-5,11-dihydroxy-4a,8,13,13-tetramethyl-4-[methyl(diphenyl)silyloxy]-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] diester
Benzaldehyde→1-Amino-4-methoxybenzene→2-Hydroxy-1-phenylethanone→2-Hydroxyacetic acid methyl ester→(2R,3S)-2-Hydroxy-3-[(4-methoxyphenyl)amino]-1,3-diphenylpropan-1-one→Methyl (2R,3S)-2-hydroxy-3-[(4-methoxyphenyl)amino]-3-phenylpropanoate→(2R,3S)-3-Phenylisoserine methyl ester→(2R,3S)-3-Amino-2-hydroxy-3-phenylpropanoic acid methyl ester hydrochloride→(4S,5R)-3-(4-Methoxyphenyl)-4-phenyl-5-(phenylcarbonyl)-1,3-oxazolidin-2-one→Methyl (4S,5R)-3-(4-methoxyphenyl)-2-oxo-4-phenyl-1,3-oxazolidine-5-carboxylate→(4S,5R)-4-Phenyl-5-(phenylcarbonyl)-1,3-oxazolidin-2-one→Methyl (4S,5R)-2-oxo-4-phenyl-1,3-oxazolidine-5-carboxylate→Phenyl (4S,5R)-2-oxo-4-phenyl-1,3-oxazolidine-5-carboxylate→(2R,3S)-3-Amino-2-hydroxy-3-phenylpropanoic acid→Bis(1,1-dimethylethyl) dicarbonoate→3(S)-(tert-Butoxycarbonylamino)-2(R)-hydroxy-3-phenylpropionic acid methyl ester→Methyl (2R,3S)-2-hydroxy-3-phenyl-3-[[(1S)-1-phenylethyl]amino]propanoate
(2alpha,5beta,7beta,10beta,13alpha)-4-(Acetyloxy)-1,7,10,13-tetrahydroxy-9-oxo-5,20-epoxytax-11-en-2-yl benzoate→Benzoic acid (3R,7R,12R)-4(S)-(acetyloxy)-1(S),15(S)-dihydroxy-10(S),14,17,17-tetramethyl-11-oxo-9(S),12(R)-bis[(2(S)2,2,2-trichloroacetyl)oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl ester→(4S,5R)-4-Phenyl-2-(tribromomethyl)-1,3-oxazolidine-5-carboxylic acid→(2alpha,5beta,7beta,10beta,13alpha)-4-(Acetyloxy)-1-hydroxy-9-oxo-2-[(phenylcarbonyl)oxy]-7,10-bis[(trichloroacetyl)oxy]-5,20-epoxytax-11-en-13-yl (4S,5R)-4-phenyl-2-(tribromomethyl)-1,3-oxazolidine-5-carboxylate→(2alpha,5beta,7beta,10beta,13alpha)-4-(Acetyloxy)-13-[[(2R,3S)-3-amino-2-hydroxy-3-phenylpropanoyl]oxy]-1-hydroxy-9-oxo-7,10-bis[(trichloroacetyl)oxy]-5,20-epoxytax-11-en-2-yl benzoate→Bis(1,1-dimethylethyl) dicarbonoate→(2alpha,5beta,7beta,10beta,13alpha)-4-(Acetyloxy)-13-([(2R,3S)-3-[(tert-butoxycarbonyl)amino]-2-hydroxy-3-phenylpropanoyl]oxy)-1-hydroxy-9-oxo-7,10-bis[(trichloroacetyl)oxy]-5,20-epoxytax-11-en-2-yl benzoate→(2R,3S)-3-Phenylisoserine methyl ester→Tribromoacetaldehyde→Methyl (4S,5R)-4-phenyl-2-(tribromomethyl)-1,3-oxazolidine-5-carboxylate
Cefcamate Pivoxil HydrochlorideOptimised routesteps: 3total yield: 48.6g(Cefcamate Pivoxil Hydrochloride-004)
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