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【结 构 式】 
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【分子编号】58021 【品名】(1R,2R,3R)-2-(benzoyloxy)-1-[(1R)-1,2-dihydroxyethyl]-3,4-dihydroxybutyl benzoate 【CA登记号】 |
【 分 子 式 】C20H22O8 【 分 子 量 】390.38988 【元素组成】C 61.53% H 5.68% O 32.79% |
合成路线1
该中间体在本合成路线中的序号：(III)Esterification of diisopropylidene mannitol (I) with benzoyl chloride in pyridine afforded dibenzoate (II). Hydrolysis of the isopropylidene ketals of (II) with aqueous HOAc gave tetraol (III), which was further converted to tetramesylate (IV) on treatment with methanesulfonyl chloride and pyridine. Reductive elimination of the mesylate groups of (IV) using Zn dust and NaI yielded diene (V). The benzoate esters of (V) were then removed by treatment with sodium methoxide. The resultant divinylglycol (VI) was reacted with dibutyltin oxide to produce the tin derivative (VII), which was converted to the target intermediate, themono-benzyl ether (VIII), by treatment with benzyl bromide in hot DMF.
| 【1】 Rao, A.V.R.; et al.; Synthesis of (3R,4R)-1,5-hexadien-3,4-diol and its unsymmetrical derivatives: Application to (R)-(+)-alpha-lipoic acid. Tetrahedron Lett 1987, 28, 19, 2183. |
| 【2】 Yadav, J.S.; et al.; Synthesis of (3R,4R)-1,2-divinylglycol and its unsymmetrical derivatives: An application to the synthesis of R-(+)-alpha lipoic acid. J Carbohydr Chem 1990, 9, 2-3, 307. |
| 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) | 45944 | (1S,2S)-1,2-bis[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-1,2-ethanediol | 1707-77-3 | C12H22O6 | 详情 | 详情 |
| (II) | 58020 | (1R,2R)-2-(benzoyloxy)-1,2-bis[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]ethyl benzoate | C26H30O8 | 详情 | 详情 | |
| (III) | 58021 | (1R,2R,3R)-2-(benzoyloxy)-1-[(1R)-1,2-dihydroxyethyl]-3,4-dihydroxybutyl benzoate | C20H22O8 | 详情 | 详情 | |
| (IV) | 58022 | (1S,2S,3R)-2-(benzoyloxy)-1-{(1R)-1,2-bis[(methylsulfonyl)oxy]ethyl}-3,4-bis[(methylsulfonyl)oxy]butyl benzoate | C24H30O16S4 | 详情 | 详情 | |
| (V) | 58023 | (1R,2R)-2-(benzoyloxy)-1-vinyl-3-butenyl benzoate | C20H18O4 | 详情 | 详情 | |
| (VI) | 58024 | (3R,4R)-1,5-hexadiene-3,4-diol | C6H10O2 | 详情 | 详情 | |
| (VII) | 58025 | (4R,5R)-2,2-dibutoxy-4,5-divinyl-1,3,2-dioxastannolane | C14H26O4Sn | 详情 | 详情 | |
| (VIII) | 58004 | (3R,4R)-4-(benzyloxy)-1,5-hexadien-3-ol | C13H16O2 | 详情 | 详情 |