　 -Drug Synthesis Database

【结构式】

【分子编号】53823

【品名】　

【CA登记号】n/a

【分子式】C₃₃H₅₆O₇

【分子量】564.80344

【元素组成】C 70.18% H 9.99% O 19.83%

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：(CXLVII)

Intermediate (CXXXIX) has been prepared by a new synthetic procedure:The known methyl 3-keto-5-alpha-chenodeoxycholanate (CXL) was protected as the methoxymethyl ether (CXLI) by treatment with dimethoxymethane and P2O5. Further protection of the keto group of (CXLI) as the ethylene ketal (CXLII), followed by reduction with LiAlH4, afforded alcohol (CXLIII). Swern oxidation of alcohol (CXLIII) yielded aldehyde (CXLIV). This was subjected to Wittig condensation with isopropylidene triphenylphosphorane to give olefin (CXLV). Sharpless asymmetric dihydroxylation of olefin (CXLV) furnished the target diol (CXLVI). Selective esterification of the secondary alcohol of (CXLVI) with Ac2O in pyridine gave rise to acetate (CXLVII).

参考文献中间体

合成目标

【1】 Zhou, X.D.; et al.; A new highly stereoselective construction of the sidechain of squalamine through improved Sharpless catalytic asymmetric dihydroxylation. Tetrahedron Lett 2001, 42, 13, 2537.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(CXL)	53816	methyl (4R)-4-[(5S,7R,8R,9S,10S,13R,14S,17R)-7-hydroxy-10,13-dimethyl-3-oxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoate	n/a	C₂₅H₄₀O₄	详情	详情
(CXLI)	53817	methyl (4R)-4-[(5S,7R,8R,9S,10S,13R,14S,17R)-7-(methoxymethoxy)-10,13-dimethyl-3-oxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoate	n/a	C₂₇H₄₄O₅	详情	详情
(CXLII)	53818		n/a	C₂₉H₄₈O₆	详情	详情
(CXLIII)	53819		n/a	C₂₈H₄₈O₅	详情	详情
(CXLIV)	53820		n/a	C₂₈H₄₆O₅	详情	详情
(CXLV)	53821		n/a	C₃₁H₅₂O₄	详情	详情
(CXLVI)	53822		n/a	C₃₁H₅₄O₆	详情	详情
(CXLVII)	53823		n/a	C₃₃H₅₆O₇	详情	详情

合成路线2

该中间体在本合成路线中的序号：(CXLVII)

The tertiary alcohol group of (CXLVII) was dehydrated to (CXLVIII) upon treatment with methanesulfonyl chloride and triethylamine. Diimide reduction of the olefin double bond of (CXLVIII) produced (CXLIX). The acetate ester of (CXLIX) was further hydrolyzed to alcohol (CL) by methanolic KOH. Then, acidic hydrolysis of the ketal protecting groups of (CL) furnished the key precursor (CXXXIX).

参考文献中间体

合成目标

【1】 Zhou, X.D.; et al.; A new highly stereoselective construction of the sidechain of squalamine through improved Sharpless catalytic asymmetric dihydroxylation. Tetrahedron Lett 2001, 42, 13, 2537.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(CXXXIX)	53815	(5S,7R,8R,9S,10S,13R,14S,17R)-7-hydroxy-17-[(1R,4R)-4-hydroxy-1,5-dimethylhexyl]-10,13-dimethylhexadecahydro-3H-cyclopenta[a]phenanthren-3-one	n/a	C₂₇H₄₆O₃	详情	详情
(CXLVII)	53823		n/a	C₃₃H₅₆O₇	详情	详情
(CXLVIII)	53824		n/a	C₃₃H₅₄O₆	详情	详情
(CXLIX)	53825		n/a	C₃₃H₅₆O₆	详情	详情
(CL)	53826		n/a	C₃₁H₅₄O₅	详情	详情

Extended Information