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CAS 115437-19-9

(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

Codes: (XIV)101438-5-a, (V)101438-8-a, (III)101438-9-a, (XIIb)101438-13-a, (VIII)101438-48-b

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)

DrugTierExpiry
Paclitaxel/Encequidar mesylateTier C — Watch / trade-
PaclitaxelTier 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.

Paclitaxel/Encequidar mesylateOptimised routesteps: 2total yield: /
1-Benzoyl-3(R)-(1-ethoxyethoxy)-4(S)-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→(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
Paclitaxel/Encequidar mesylateOptimised routesteps: 4total yield: /
13-Acetyl-9-dihydrobaccatin-III→(2aR,4S,4aR,5R,6R,9S,11S,12S,12aR,12bS)-9,12b-Bis(acetoxy)-5,6,11-trihydroxy-4a,8,13,13-tetramethyl-4-[triethylsilyloxy]-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,9S,11S,12S,12aR,12bS)-9,12b-Bis(acetoxy)-11-hydroxy-4a,8,13,13-tetramethyl-5,6-dioxo-4-[triethylsilyloxy]-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,9S,11S,12S,12aR,12bS)-12b-(Acetoxy-9,11-dihydroxy-4a,8,13,13-tetramethyl-5,6-dioxo-4-[triethylsilyloxy]-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→3(S)-(Benzamido)-2(R)-(1-ethoxyethoxy)-3-phenylpropionic acid→1-Benzoyl-3(R)-(1-ethoxyethoxy)-4(S)-phenylazetidin-2-one→(2aR,4S,4aS,9S,11S,12S,12aR,12bS)-12b-(Acetyloxy)-9-[3(S)-(benzamido)-2(R)-(1-ethoxyethoxy)-3-phenylpropanoyloxy]-11-hydroxy-4a,8,13,13-tetramethyl-5,6-dioxo-4-[triethylsilyloxy]-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-[3(S)-(benzamido)-2(R)-(1-ethoxyethoxy)-3-phenylpropanoyloxy]-6,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-4-[triethylsilyloxy]-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→(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
Paclitaxel/Encequidar mesylateOptimised routesteps: 3total yield: /
(2aR,4S,4aS,9S,11S,12S,12aR,12bS)-12b-(Acetyloxy)-9-[3(S)-(benzamido)-2(R)-(1-ethoxyethoxy)-3-phenylpropanoyloxy]-11-hydroxy-4a,8,13,13-tetramethyl-5,6-dioxo-4-[triethylsilyloxy]-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-[3(S)-(benzamido)-2(R)-(1-ethoxyethoxy)-3-phenylpropanoyloxy]-6,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-4-[triethylsilyloxy]-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→(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
PaclitaxelOptimised routesteps: 2total yield: /
1-Benzoyl-3(R)-(1-ethoxyethoxy)-4(S)-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→(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
PaclitaxelOptimised routesteps: 4total yield: /
13-Acetyl-9-dihydrobaccatin-III→(2aR,4S,4aR,5R,6R,9S,11S,12S,12aR,12bS)-9,12b-Bis(acetoxy)-5,6,11-trihydroxy-4a,8,13,13-tetramethyl-4-[triethylsilyloxy]-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,9S,11S,12S,12aR,12bS)-9,12b-Bis(acetoxy)-11-hydroxy-4a,8,13,13-tetramethyl-5,6-dioxo-4-[triethylsilyloxy]-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,9S,11S,12S,12aR,12bS)-12b-(Acetoxy-9,11-dihydroxy-4a,8,13,13-tetramethyl-5,6-dioxo-4-[triethylsilyloxy]-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→3(S)-(Benzamido)-2(R)-(1-ethoxyethoxy)-3-phenylpropionic acid→1-Benzoyl-3(R)-(1-ethoxyethoxy)-4(S)-phenylazetidin-2-one→(2aR,4S,4aS,9S,11S,12S,12aR,12bS)-12b-(Acetyloxy)-9-[3(S)-(benzamido)-2(R)-(1-ethoxyethoxy)-3-phenylpropanoyloxy]-11-hydroxy-4a,8,13,13-tetramethyl-5,6-dioxo-4-[triethylsilyloxy]-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-[3(S)-(benzamido)-2(R)-(1-ethoxyethoxy)-3-phenylpropanoyloxy]-6,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-4-[triethylsilyloxy]-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→(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
PaclitaxelOptimised routesteps: 3total yield: /
(2aR,4S,4aS,9S,11S,12S,12aR,12bS)-12b-(Acetyloxy)-9-[3(S)-(benzamido)-2(R)-(1-ethoxyethoxy)-3-phenylpropanoyloxy]-11-hydroxy-4a,8,13,13-tetramethyl-5,6-dioxo-4-[triethylsilyloxy]-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-[3(S)-(benzamido)-2(R)-(1-ethoxyethoxy)-3-phenylpropanoyloxy]-6,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-4-[triethylsilyloxy]-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→(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

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