4-(acetyloxy)-1,9,12,15-tetrahydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0~3,10~.0~4,7~]heptadec-13-en-2-yl benzoate -Drug Synthesis Database

【结构式】

【分子编号】64863

【品名】4-(acetyloxy)-1,9,12,15-tetrahydroxy-10,14,17,17-tetramethyl-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】C₂₉H₃₆O₁₀

【分子量】544.59884

【元素组成】C 63.96% H 6.66% O 29.38%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(I)

Protection of 10-deacetylbaccatin III (I) with chlorotriethylsilane in pyridine affords the 7,13-bis-silyl ether (II), which upon alkylation by means of iodomethane and NaH provides the 10-methoxy derivative (III). After desilylation of (III) by means of a hydrogen fluoride-triethylamine complex, the deprotected triol (IV) is methylated with iodomethane and NaH to yield the 7,10-dimethyl ether (V). Esterification of (V) with the oxazolidinecarboxylic acid (VI) in the presence of DCC/DMAP furnishes (VII). (1,2)

参考文献中间体

合成目标

【1】 Bouchard, H.; Bourzat, J.-D.; Commerçon, A. (Aventis Pharma SA); Novel taxoids, preparation thereof and pharmaceutical compsns. containing same. EP 0817779; EP 0817780; FR 2732340; JP 1999500141; JP 1999502531; US 5889043; US 6372780; US 6387946; WO 9630355; WO 9630356 .
【2】 Bissery, M.-C. (Aventis Pharma SA); Use of taxoid derivs.. EP 1020188; EP 1140064; US 2002082291; US 6403634; WO 0041482 .

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	64863	4-(acetyloxy)-1,9,12,15-tetrahydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0~3,10~.0~4,7~]heptadec-13-en-2-yl benzoate	C₂₉H₃₆O₁₀	详情	详情
(II)	64864		C₄₁H₆₄O₁₀Si₂	详情	详情
(III)	64865		C₄₂H₆₆O₁₀Si₂	详情	详情
(IV)	64866		C₃₀H₃₈O₁₀	详情	详情
(V)	64867		C₃₁H₄₀O₁₀	详情	详情
(VI)	64868	3-{[(1,1-dimethylethyl)oxy]carbonyl}-2-[4-(methyloxy)phenyl]-4-phenyl-1,3-oxazolidine-5-carboxylic acid	C₂₂H₂₅NO₆	详情	详情
(VII)	64869		C₅₃H₆₃NO₁₅	详情	详情

合成路线2

该中间体在本合成路线中的序号：(I)

参考文献中间体

合成目标

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)	64863	4-(acetyloxy)-1,9,12,15-tetrahydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0~3,10~.0~4,7~]heptadec-13-en-2-yl benzoate		C₂₉H₃₆O₁₀	详情	详情
(II)	64867			C₃₁H₄₀O₁₀	详情	详情
(III)	54908	(2R,3S)-3-amino-2-hydroxy-3-phenylpropanoic acid	136561-53-0	C₉H₁₁NO₃	详情	详情
(IV)	67065	(2R,3S)-3-((tert-butoxycarbonyl)amino)-2-hydroxy-3-phenylpropanoic acid		C₁₄H₁₉NO₅	详情	详情

Extended Information