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【结 构 式】 
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【分子编号】46173 【品名】ethyl (4S,5R)-5-[3-(benzyloxy)propyl]-2,2,4-trimethyl-1,3-dioxolane-4-carboxylate 【CA登记号】 |
【 分 子 式 】C19H28O5 【 分 子 量 】336.42832 【元素组成】C 67.83% H 8.39% O 23.78% |
合成路线1
该中间体在本合成路线中的序号：(XIII)Synthesis of intermediate aldehyde (XV): The oxidation of 4-(benzyloxy)butanol (VIII) with oxalyl chloride gives the aldehyde (IX), which is condensed with 2-(triphenylphosphoranylidene)propionic acid ethyl ester (X) in hot THF to yield the unsaturated ester (XI). The enantioselective dihydroxylation of (XI) by means of AD-mix beta and methanesulfonamide in butanol/water affords the chiral dihydroxyester (XII), which is protected with 2,2-dimethoxypropane and CSA to provide the acetonide (XIII). The reduction of the ester group of (XIII) with DIBAL in THF gives the alcohol (XIV), which is finally oxidized with DMP to yield the desired intermediate aldehyde (XV).
| 【1】 Mulzer, J.; et al.; A novel highly stereoselective total synthesis of epothilone B and of its (12R,13R) acetonide. Tetrahedron Lett 2000, 41, 40, 7635. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (VIII) | 46169 | 4-(benzyloxy)-1-butanol | C11H16O2 | 详情 | 详情 | |
| (IX) | 46170 | 4-(benzyloxy)butanal | C11H14O2 | 详情 | 详情 | |
| (X) | 37071 | ethyl 2-(triphenylphosphoranylidene)propanoate | 5717-37-3 | C23H23O2P | 详情 | 详情 |
| (XI) | 46171 | ethyl (E)-6-(benzyloxy)-2-methyl-2-hexenoate | C16H22O3 | 详情 | 详情 | |
| (XII) | 46172 | ethyl (2S,3R)-6-(benzyloxy)-2,3-dihydroxy-2-methylhexanoate | C16H24O5 | 详情 | 详情 | |
| (XIII) | 46173 | ethyl (4S,5R)-5-[3-(benzyloxy)propyl]-2,2,4-trimethyl-1,3-dioxolane-4-carboxylate | C19H28O5 | 详情 | 详情 | |
| (XIV) | 46174 | [(4R,5R)-5-[3-(benzyloxy)propyl]-2,2,4-trimethyl-1,3-dioxolan-4-yl]methanol | C17H26O4 | 详情 | 详情 | |
| (XV) | 46175 | (4S,5R)-5-[3-(benzyloxy)propyl]-2,2,4-trimethyl-1,3-dioxolane-4-carbaldehyde | C17H24O4 | 详情 | 详情 |