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【结 构 式】 
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【分子编号】58061 【品名】ethyl (4R,5S)-5-(5-methoxy-5-oxopentyl)-2,2-dioxo-1,3,2lambda~6~-dioxathiolane-4-carboxylate 【CA登记号】 |
【 分 子 式 】C11H18O8S 【 分 子 量 】310.32512 【元素组成】C 42.58% H 5.85% O 41.25% S 10.33% |
合成路线1
该中间体在本合成路线中的序号：(XL)The olefinic diester (XXXVIII) was subjected to OsO4-catalyzed asymmetric dihydroxylation using hydroquinidine 1,4-phthalazinediyl diether [(DHQD)2-PHAL] as chiral ligand to afford diol (XXXIX). This was converted to the cyclic sulfate (XL) by treatment with SOCl2, followed by RuCl3-catalyzed NaIO4 oxidation of the intermediate sulfite. Regioselective reduction of sulfate (XL) at the alpha position with NaBH4 in DMA led to the (3S)-alcohol (XLI). Further selective reduction of the ethyl ester group of (XLI) was achieved by treatment with NaBH4-Et3N in MeOH-DMF, yielding the target intermediate dihydroxy ester (XIII).
| 【1】 Upadhya, T.T.; et al.; Asymmetric dihydroxylation and hydrogenation approaches to the enantioselective synthesis of R-(+)-alpha-lipoic acid. Tetrahedron Lett 2001, 42, 29, 4891. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XIII) | 57977 | methyl (6S)-6,8-dihydroxyoctanoate | C9H18O4 | 详情 | 详情 | |
| (XXXVIII) | 58059 | 1-ethyl 8-methyl (E)-2-octenedioate | C11H18O4 | 详情 | 详情 | |
| (XXXIX) | 58060 | 1-ethyl 8-methyl (2R,3S)-2,3-dihydroxyoctanedioate | C11H20O6 | 详情 | 详情 | |
| (XL) | 58061 | ethyl (4R,5S)-5-(5-methoxy-5-oxopentyl)-2,2-dioxo-1,3,2lambda~6~-dioxathiolane-4-carboxylate | C11H18O8S | 详情 | 详情 | |
| (XLI) | 58062 | 1-ethyl 8-methyl (3S)-3-hydroxyoctanedioate | C11H20O5 | 详情 | 详情 |