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【结 构 式】

【分子编号】63885

【品名】(E,5S)-6-{[tert-butyl(diphenyl)silyl]oxy}-5-[(4-methoxybenzyl)oxy]-2-hexen-1-ol

【CA登记号】

【 分 子 式 】C30H38O4Si

【 分 子 量 】490.71482

【元素组成】C 73.43% H 7.81% O 13.04% Si 5.72%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(XXII)

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
Extended Information