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CAS 149249-91-2
(3R,4S)-1-Benzoyl-4-phenyl-3-(triethylsiloxy)azetidin-2-one
Codes: (XXIII)101438-7-b, (XXXVII)101438-11-c, (Xa)101438-13-a, (XIV)101438-17-a, (XX)101438-24-b, (XIII)101438-34-a, (XLVIII)101438-35-d, (V)101438-43-a, (V)101438-44-a, (V)101438-64-a, (XXIX)101438-71-c, (XXVI)101438-72-d
Application context (from source-drug indications)
Breast cancerPaclitaxel/Encequidar mesylateAdenocarcinomaPaclitaxel/Encequidar mesylateAngiosarcomaPaclitaxel/Encequidar mesylateSolid tumourPaclitaxel/Encequidar mesylatePancreatic cancerPaclitaxelNon-small cell lung cancerPaclitaxelHodgkin's diseasePaclitaxelSeminomaPaclitaxelOvarian cancerPaclitaxelBreast cancerPaclitaxel
Source drugs (routes using this intermediate)
| Drug | Tier | Expiry |
|---|---|---|
| Paclitaxel/Encequidar mesylate | Tier C — Watch / trade | - |
| Paclitaxel | 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.
(1S,5S,6R,7S,10R,12S,13S,15R)-15-(acetyloxy)-13,17,20,20-tetramethyl-3,14-dioxo-12-[(triethylsilyl)oxy]-2,4,9-trioxapentacyclo[14.3.1.0(1,5).0(6,13).0(7,10)]icos-16-en-7-yl acetate→(1S,5S,6R,7S,8S,10S,11S,13R)-7,8,10-trihydroxy-7-(hydroxymethyl)-11,15,18,18-tetramethyl-3,12-dioxo-2,4-dioxatetracyclo[12.3.1.0(1,5).0(6,11)]octadec-14-en-13-yl acetate→[(1S,5S,6R,7S,8S,10S,11S,13R)-13-(acetyloxy)-7,8,10-trihydroxy-11,15,18,18-tetramethyl-3,12-dioxo-2,4-dioxatetracyclo[12.3.1.0(1,5).0(6,11)]octadec-14-en-7-yl]methyl acetate→(1S,5S,6R,7S,8S,10S,11S,13R)-7,8-dihydroxy-7-(hydroxymethyl)-11,15,18,18-tetramethyl-3,12-dioxo-10-[(triethylsilyl)oxy]-2,4-dioxatetracyclo[12.3.1.0(1,5).0(6,11)]octadec-14-en-13-yl acetate→(1S,5S,6R,7S,10R,12S,13S,15R)-7-hydroxy-13,17,20,20-tetramethyl-3,14-dioxo-12-[(triethylsilyl)oxy]-2,4,9-trioxapentacyclo[14.3.1.0(1,5).0(6,13).0(7,10)]icos-16-en-15-yl acetate→(1S,2S,3R,4S,7R,9S,10S,12R)-4,12-bis(acetyloxy)-1-hydroxy-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→(1S,2S,3R,4S,7R,9S,10S,12R)-4,12-bis(acetyloxy)-1-hydroxy-10,14,17,17-tetramethyl-11,15-dioxo-9-[(triethylsilyl)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)-1,15-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→(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-[(triethylsilyl)oxy]-5,20-epoxytax-11-en-2-yl benzoate
(1S,5S,6R,7S,10R,12S,13R,15R,18S)-12-[(benzyloxy)methyl]-18-[(tert-butyldimethylsilyl)oxy]-15-hydroxy-13,17,20,20-tetramethyl-3-oxo-2,4,9-trioxapentacyclo[14.3.1.0(1,5).0(6,13).0(7,10)]icos-16-en-7-yl acetate→(1S,2S,3R,4S,7R,9S,10R,15S)-4-(acetyloxy)-9-[(benzyloxy)methyl]-15-[(tert-butyldimethylsilyl)oxy]-1-hydroxy-10,14,17,17-tetramethyl-12-oxo-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate→potassium (1S,2S,3R,4S,7R,9S,10S,11E,15S)-4-(acetyloxy)-2-(benzoyloxy)-9-[(benzyloxy)methyl]-15-[(tert-butyldimethylsilyl)oxy]-1-hydroxy-10,14,17,17-tetramethyl-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadeca-11,13-dien-12-olate→(1S,2S,3R,4S,7R,9S,10R,12R,15S)-4,12-bis(acetyloxy)-9-[(benzyloxy)methyl]-15-[(tert-butyldimethylsilyl)oxy]-1-hydroxy-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)-4,10-Bis(acetyloxy)-7-[(benzyloxy)methyl]-1,13-dihydroxy-9-oxo-5,20-epoxytax-11-en-2-yl benzoate→(3R,4S)-1-Benzoyl-4-phenyl-3-(triethylsiloxy)azetidin-2-one→(1S,2S,3R,4S,7R,9S,10R,12R,15S)-4,12-bis(acetyloxy)-9-[(benzyloxy)methyl]-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-15-{[(2R,3S)-3-phenyl-3-(phenylformamido)-2-[(triethylsilyl)oxy]propanoyl]oxy}-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate
(3R,4S)-4-Phenyl-3-[(triethylsilyl)oxy]azetidin-2-one→(NZ)-4-Methoxy-N-(phenylmethylidene)aniline→1-Amino-4-methoxybenzene→1-Benzoyl-3(R)-(1-ethoxyethoxy)-4(S)-phenylazetidin-2-one→alpha-Chlorobenzaldehyde→Benzaldehyde→cis-1-(4-Methoxyphenyl)-2-oxo-4-phenylazetidin-3-yl acetate→cis-2-Oxo-4-phenylazetidin-3-yl acetate→(3R,4S)-1-Benzoyl-4-phenyl-3-(triethylsiloxy)azetidin-2-one→(3R,4S)-3-(1-Ethoxyethoxy)-4-phenylazetidin-2-one→(3R,4S)-3-hydroxy-4-phenylazetidin-2-one→(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→(2-Chloranyl-2-oxidanylideneethyl) ethanoate→(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)-4,10-Diacetoxy-13-[[(2R,3S)-3-(benzoylamino)-2-(1-ethoxyethoxy)-3-phenylpropanoyl]oxy]-1-hydroxy-9-oxo-7-[(triethylsilyl)oxy]-5,20-epoxytax-11-en-2-yl benzoate
Methyl L-threoninate hydrogen chloride→methyl (2S,3R)-2-amino-3-{[(tert-butoxy)diphenylsilyl]oxy}butanoate→[formyl-[14]C]Benzaldehyde→methyl (2S,3R)-3-[(tert-butyldiphenylsilyl)oxy]-2-[(E)-(phenylmethylidene)amino]butanoate→methyl 2-[(3S,4S)-3-(acetyloxy)-2-oxo-4-phenylazetidin-1-yl]-2-oxoacetate→(2-Chloranyl-2-oxidanylideneethyl) ethanoate→methyl (2S,3R)-2-[(3R,4S)-3-(acetyloxy)-2-oxo-4-phenylazetidin-1-yl]-3-[(tert-butyldiphenylsilyl)oxy]butanoate→methyl (2S,3R)-2-[(3R,4S)-3-(acetyloxy)-2-oxo-4-phenylazetidin-1-yl]-3-hydroxybutanoate→methyl (2Z)-2-[(3R,4S)-3-(acetyloxy)-2-oxo-4-phenylazetidin-1-yl]but-2-enoate→methyl 2-[(3R,4S)-3-(acetyloxy)-2-oxo-4-phenylazetidin-1-yl]-2-oxoacetate→(3S,4S)-2-oxo-4-phenylazetidin-3-yl acetate→(3S,4S)-3-hydroxy-4-phenylazetidin-2-one→(3S,4S)-4-phenyl-3-[(triethylsilyl)oxy]azetidin-2-one→alpha-Chlorobenzaldehyde→(3R,4S)-1-Benzoyl-4-phenyl-3-(triethylsiloxy)azetidin-2-one→(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→(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetyloxy)-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-15-{[(2S,3S)-3-phenyl-3-(phenylformamido)-2-[(triethylsilyl)oxy]propanoyl]oxy}-9-[(triethylsilyl)oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate→[2aR-(2aalpha,4beta,4abeta,6beta,9alpha(2R,3S),11beta,12alpha,12aalpha,12balpha]-6-Acetoxy-9-[3-(4-deuterobenzamido)-2-hydroxy-3-phenylpropionyloxy]-12-(benzoyloxy)-12b-(trideuteroacetoxy)-4,11-dihydroxy-4a,8,13,13-tetramethyl-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-1H-7,11-methanocyclodeca[3,4]benz[1,2-b]oxet- 5-one→(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-hydroxy-10,14,17,17-tetramethyl-11-oxo-15-[(tributylsilyl)oxy]-9-[(triethylsilyl)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-10,14,17,17-tetramethyl-11-oxo-15-[(tributylsilyl)oxy]-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,3S,5S,6R,7S,10R,12S,13S,15R,18S)-7-hydroxy-13,17,20,20-tetramethyl-14-oxo-3-phenyl-18-[(tributylsilyl)oxy]-12-[(triethylsilyl)oxy]-2,4,9-trioxapentacyclo[14.3.1.0(1,5).0(6,13).0(7,10)]icos-16-en-15-yl acetate→(1S,5S,6R,7S,10R,12S,13S,15R,18S)-7-hydroxy-13,17,20,20-tetramethyl-3,14-dioxo-18-[(tributylsilyl)oxy]-12-[(triethylsilyl)oxy]-2,4,9-trioxapentacyclo[14.3.1.0(1,5).0(6,13).0(7,10)]icos-16-en-15-yl acetate→(3R,4S)-1-Benzoyl-4-phenyl-3-(triethylsiloxy)azetidin-2-one
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