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【结 构 式】 
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【分子编号】47093 【品名】(4R,5S,6S)-9-(benzyloxy)-2-[(4S)-2,2-dimethyl-1,3-dioxan-4-yl]-5-hydroxy-2,4,6-trimethyl-3-nonanone 【CA登记号】 |
【 分 子 式 】C25H40O5 【 分 子 量 】420.5896 【元素组成】C 71.39% H 9.59% O 19.02% |
合成路线1
该中间体在本合成路线中的序号：(III)The intermediate olefin (XI) was prepared as follows. The diastereoselective aldol condensation between aldehyde (I) and ketone (II) provided the desired aldol diastereoisomer (III). Acetonide hydrolysis in (III) by means of pyridinium tosylate in MeOH, followed by protection of the resultant triol with tert-butyl-dimethylsilyl triflate, gave the tris-silyl ether (IV). The primary hydroxyl group of (IV) was then selectively deprotected by treatment with camphorsulfonic acid, yielding alcohol (V). Swern oxidation of (V) produced aldehyde (VI), which was further oxidized to carboxylic acid (VII) by means of sodium chlorite.
| 【1】 Altmann, K.-H.; et al.; Synthesis and biological evaluation of highly potent analogues of epothilones B and D. Bioorg Med Chem Lett 2000, 10, 24, 2765. |
| 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) | 47092 | (2S)-5-(benzyloxy)-2-methylpentanal | C13H18O2 | 详情 | 详情 | |
| (II) | 27176 | 2-[(4S)-2,2-dimethyl-1,3-dioxan-4-yl]-2-methyl-3-pentanone | C12H22O3 | 详情 | 详情 | |
| (III) | 47093 | (4R,5S,6S)-9-(benzyloxy)-2-[(4S)-2,2-dimethyl-1,3-dioxan-4-yl]-5-hydroxy-2,4,6-trimethyl-3-nonanone | C25H40O5 | 详情 | 详情 | |
| (IV) | 47094 | (5S,6R,9S)-5-[(1S)-4-(benzyloxy)-1-methylbutyl]-9-[[tert-butyl(dimethyl)silyl]oxy]-2,2,3,3,6,8,8,13,13,14,14-undecamethyl-4,12-dioxa-3,13-disilapentadecan-7-one | C40H78O5Si3 | 详情 | 详情 | |
| (V) | 47095 | (5S,8R,9S)-9-[(1S)-4-(benzyloxy)-1-methylbutyl]-5-(2-hydroxyethyl)-2,2,3,3,6,6,8,11,11,12,12-undecamethyl-4,10-dioxa-3,11-disilatridecan-7-one | C34H64O5Si2 | 详情 | 详情 | |
| (VI) | 47096 | (3S,6R,7S,8S)-11-(benzyloxy)-3,7-bis[[tert-butyl(dimethyl)silyl]oxy]-4,4,6,8-tetramethyl-5-oxoundecanal | C34H62O5Si2 | 详情 | 详情 | |
| (VII) | 47097 | (3S,6R,7S,8S)-11-(benzyloxy)-3,7-bis[[tert-butyl(dimethyl)silyl]oxy]-4,4,6,8-tetramethyl-5-oxoundecanoic acid | C34H62O6Si2 | 详情 | 详情 |