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【结 构 式】 
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【分子编号】53822 【品名】 【CA登记号】n/a |
【 分 子 式 】C31H54O6 【 分 子 量 】522.76616 【元素组成】C 71.23% H 10.41% O 18.36% |
合成路线1
该中间体在本合成路线中的序号：(CXLVI)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).
| 【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 |