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【结 构 式】

【分子编号】57331

【品名】(2S,3S)-1-{[tert-butyl(diphenyl)silyl]oxy}-3-(1,3-dithian-2-yl)-2-butanol

【CA登记号】

【 分 子 式 】C24H34O2S2Si

【 分 子 量 】446.75026

【元素组成】C 64.52% H 7.67% O 7.16% S 14.36% Si 6.29%

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:(V)

Synthesis of the intermediate butyraldehyde (X): The Sharpless asymmetric epoxidation of 2(E)-buten-1-ol by means of t-Bu-OOH and D-(-9-diisopropyl tartrate gives the epoxy alcohol (II), which is treated with Tbdps-Cl, TEA and DMAP to yield the silyl ether (III) The condensation of (III) with 1,3-dithiane (IV) by means of BuLi in THF/HMPA affords the cyclic thioketal (V), which is deprotected by means of TBAF in THF, affording the diol (VI). The reaction of (VI) with 4-methoxybenzaldehyde dimethylacetal (VII) by means of TsOH in DMF provides the benzylidene ketal (VIII), which is submitted to a selective opening by means of DIBAL in dichloromethane to give the secondary benzyl ether (IX). Finally this compound is oxidized with SO3/Pyridine and TEA in DMSO/dichloromethane to obtain the target intermediate, the chiral butyraldehyde (X).

1 Chen, K.; Formal total synthesis of (-)-FK506. Diss Abstr Int B - Sci Eng 1993, 53, 9, 4663.
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) 54882 2-Butene-1-ol; Crotyl Alcohol; trans-Propenylcarbinol 504-61-0 C4H8O 详情 详情
(II) 57330 [(2R,3R)-3-methyloxiranyl]methanol C4H8O2 详情 详情
(III) 14956 tert-butyl[[(2R,3R)-3-methyloxiranyl]methoxy]diphenylsilane; tert-butyl(diphenyl)silyl [(2R,3R)-3-methyloxiranyl]methyl ether C20H26O2Si 详情 详情
(IV) 42372 1,3-dithiane 505-23-7 C4H8S2 详情 详情
(V) 57331 (2S,3S)-1-{[tert-butyl(diphenyl)silyl]oxy}-3-(1,3-dithian-2-yl)-2-butanol C24H34O2S2Si 详情 详情
(VI) 57332 (2S,3S)-3-(1,3-dithian-2-yl)-1,2-butanediol C8H16O2S2 详情 详情
(VII) 26485 1-(dimethoxymethyl)-4-methoxybenzene 2186-92-7 C10H14O3 详情 详情
(VIII) 57333 (4S)-4-[(1S)-1-(1,3-dithian-2-yl)ethyl]-2-(4-methoxyphenyl)-1,3-dioxolane; 4-{(4S)-4-[(1S)-1-(1,3-dithian-2-yl)ethyl]-1,3-dioxolan-2-yl}phenyl methyl ether C16H22O3S2 详情 详情
(IX) 57334 (2S,3S)-3-(1,3-dithian-2-yl)-2-[(4-methoxybenzyl)oxy]-1-butanol C16H24O3S2 详情 详情
(X) 57335 (2S,3S)-3-(1,3-dithian-2-yl)-2-[(4-methoxybenzyl)oxy]butanal C16H22O3S2 详情 详情
Extended Information