(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetoxy)-15-[[(2R,3S)-3-(benzoylamino)-2-([2-[(4S)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]acetyl]oxy)-3-phenylpropanoyl]oxy]-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)] -Drug Synthesis Database

【结构式】

【分子编号】39222

【品名】(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetoxy)-15-[[(2R,3S)-3-(benzoylamino)-2-([2-[(4S)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]acetyl]oxy)-3-phenylpropanoyl]oxy]-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]

【CA登记号】

【分子式】C₅₄H₅₉NO₁₈

【分子量】1010.0584

【元素组成】C 64.21% H 5.89% N 1.39% O 28.51%

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)

Malic acid (I) was protected as the 1,2-O-isopropylidene derivative (II) upon treatment with acetone in the presence of acid catalyst. Condensation of (II) with paclitaxel (III) using diisopropylcarbodiimide and DMAP produced the 2'-ester (IV). After hydrolytic cleavage of the isopropylidene protecting group of (IV), conversion to the corresponding sodium carboxylate salt furnished the title compound.

参考文献中间体

合成目标

【1】 Braamer, L.; Damen, E.W.P.; Wiegerinck, P.H.G.; Sperling, D.; de Vos, D.; Scheren, H.W.; Paclitaxel esters of malic acid as prodrugs with improved water solubility. Bioorg Med Chem 2000, 8, 2, 427.
【2】 Wiegerinck, P.H.G.; Scheeren, J.W.; Damen, E.W.P.; Sperling, D.; Braamer, L.; De Vos, D. (Pharmachemie BV); Water soluble analogs and prodrugs of paclitaxel. WO 0010988 .

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)	11058	(S)-(+)-Hydroxysuccinic acid; (S)-(+)-Malic acid; (S)-(+)-2-Hydroxybutanedioic acid; L-(-)-Apple acid	97-67-6	C₄H₆O₅	详情	详情
(II)	39221	2-[(4S)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]acetic acid	73991-95-4	C₇H₁₀O₅	详情	详情
(III)	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
(IV)	39222	(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetoxy)-15-[[(2R,3S)-3-(benzoylamino)-2-([2-[(4S)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]acetyl]oxy)-3-phenylpropanoyl]oxy]-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]		C₅₄H₅₉NO₁₈	详情	详情

Extended Information