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【结 构 式】

【分子编号】58360

【品名】(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetyloxy)-15-[((2R,3S)-3-(benzoylamino)-3-phenyl-2-{[(2,2,2-trichloroethoxy)carbonyl]oxy}propanoyl)oxy]-1-hydroxy-10,14,17,17-tetramethyl-9-({3-methyl-3-[(2,4,6-trimethoxybenzyl)sulfanyl]butanoyl}oxy)-11-oxo-6-oxatetracyclo[11.3.1.0~3,10~.0~4,7~]heptadec-13-en-2-yl benzoate

【CA登记号】

【 分 子 式 】C65H72Cl3NO20S

【 分 子 量 】1325.70552

【元素组成】C 58.89% H 5.47% Cl 8.02% N 1.06% O 24.14% S 2.42%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(IV)

Paclitaxel (I) is selectively protected at the side-chain hydroxyl group with 2,2,2-trichloroethyl chloroformate in pyridine to afford the carbonate ester (II). Subsequent acylation of (II) with 3-methyl-3-[(2,4,6-trimethoxybenzyl)thio]butyric acid (III) provides ester (IV). Removal of the trimethoxybenzyl protecting group of (IV) by means of formic acid in the presence of L-cysteine gives rise to thiol (V).

1 Lin, C.-E.; et al.; Design and synthesis of nitrosylated paclitaxel (NO-paclitaxel) and adamantanyl nitric oxide donor as antirestenosis agents. 223rd ACS Natl Meet (April 7 2002, Orlando) 2002, Abst MEDI 36.
2 Garvey, D.S.; Letts, L.G.; Wang, T.; Richardson, S.K.; Lin, C.-E. (NitroMed Inc.); Nitrosated and nitrosylated taxanes, compsns. and methods of use. WO 0198286 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 10595 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetoxy)-15-[[(2R,3S)-3-(benzoylamino)-2-hydroxy-3-phenylpropanoyl]oxy]-1,9-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 33069-62-4 C47H51NO14 详情 详情
(II) 58359 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetyloxy)-15-[((2R,3S)-3-(benzoylamino)-3-phenyl-2-{[(2,2,2-trichloroethoxy)carbonyl]oxy}propanoyl)oxy]-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0~3,10~.0~4,7~]heptadec-13-en-2-yl C50H52Cl3NO16 详情 详情
(III) 38878 3-methyl-3-[(2,4,6-trimethoxybenzyl)sulfanyl]butyric acid C15H22O5S 详情 详情
(IV) 58360 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetyloxy)-15-[((2R,3S)-3-(benzoylamino)-3-phenyl-2-{[(2,2,2-trichloroethoxy)carbonyl]oxy}propanoyl)oxy]-1-hydroxy-10,14,17,17-tetramethyl-9-({3-methyl-3-[(2,4,6-trimethoxybenzyl)sulfanyl]butanoyl}oxy)-11-oxo-6-oxatetracyclo[11.3.1.0~3,10~.0~4,7~]heptadec-13-en-2-yl benzoate C65H72Cl3NO20S 详情 详情
(V) 58361 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetyloxy)-15-[((2R,3S)-3-(benzoylamino)-3-phenyl-2-{[(2,2,2-trichloroethoxy)carbonyl]oxy}propanoyl)oxy]-1-hydroxy-10,14,17,17-tetramethyl-9-[(3-methyl-3-sulfanylbutanoyl)oxy]-11-oxo-6-oxatetracyclo[11.3.1.0~3,10~.0~4,7~]heptadec-13-en-2-yl benzoate C55H60Cl3NO17S 详情 详情
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