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【结 构 式】 
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【分子编号】63886 【品名】(2S,4E)-2-[(4-methoxybenzyl)oxy]-6-(trityloxy)-4-hexen-1-ol 【CA登记号】 |
【 分 子 式 】C33H34O4 【 分 子 量 】494.63056 【元素组成】C 80.13% H 6.93% O 12.94% |
合成路线1
该中间体在本合成路线中的序号：(XXIV)The chiral unsaturated aldehyde intermediate (XXV) has been obtained as follows. The reaction of the chiral lactone (XVII) first with N,O-dimethylhydroxylamine and then with PmbO-(C=NH)CCl3 gives the Weinreb amide (XVIII), which is reduced with Bu2AlH to yield the butyraldehyde (XIX). The condensation of (XIX) with phosphorane (XX) affords the unsaturated ester (XXI), which is reduced with Bu2AlH to provide the unsaturated alcohol (XXII). The reaction of (XXII) with TrCl and lutidine gives the trityl ether (XXIII), which is desilylated by means of TBAF to yield the primary alcohol (XXIV). Finally, this compound is oxidized with DMP to afford the desired unsaturated aldehyde intermediate (XXV).
| 【1】 Nelson, S.G.; Cheung, W.S.; Kassick, A.J.; Hilfiker, M.A.; A de novo enantioselective total synthesis of (-)-laulimalide. J Am Chem Soc 2002, 124, 46, 13654. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 63307 | 1,1,1-trichloro-3-(4-methoxyphenyl)-2-propanimine | C10H10Cl3NO | 详情 | 详情 | ||
| (XVII) | 63880 | 4-{[tert-butyl(diphenyl)silyl]oxy}-2-oxetanone | C19H22O3Si | 详情 | 详情 | |
| (XVIII) | 63881 | (3S)-4-{[tert-butyl(diphenyl)silyl]oxy}-N-methoxy-3-[(4-methoxybenzyl)oxy]-N-methylbutanamide | C30H39NO5Si | 详情 | 详情 | |
| (XIX) | 63882 | (3S)-4-{[tert-butyl(diphenyl)silyl]oxy}-3-[(4-methoxybenzyl)oxy]butanal | C28H34O4Si | 详情 | 详情 | |
| (XX) | 14182 | ethyl 2-(triphenyl-lambda(5)-phosphanylidene)acetate; (Carbethoxymethylene)triphenylphosphorane | 1099-45-2 | C22H21O2P | 详情 | 详情 |
| (XXI) | 63884 | ethyl (E,5S)-6-{[tert-butyl(diphenyl)silyl]oxy}-5-[(4-methoxybenzyl)oxy]-2-hexenoate | C32H40O5Si | 详情 | 详情 | |
| (XXII) | 63885 | (E,5S)-6-{[tert-butyl(diphenyl)silyl]oxy}-5-[(4-methoxybenzyl)oxy]-2-hexen-1-ol | C30H38O4Si | 详情 | 详情 | |
| (XXIII) | 63883 | tert-butyl(diphenyl)silyl (2S,4E)-2-[(4-methoxybenzyl)oxy]-6-(trityloxy)-4-hexenyl ether; tert-butyl{[(2S,4E)-2-[(4-methoxybenzyl)oxy]-6-(trityloxy)-4-hexenyl]oxy}diphenylsilane | C49H52O4Si | 详情 | 详情 | |
| (XXIV) | 63886 | (2S,4E)-2-[(4-methoxybenzyl)oxy]-6-(trityloxy)-4-hexen-1-ol | C33H34O4 | 详情 | 详情 | |
| (XXV) | 63887 | (2S,4E)-2-[(4-methoxybenzyl)oxy]-6-(trityloxy)-4-hexenal | C33H32O4 | 详情 | 详情 |