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【结 构 式】 
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【分子编号】40840 【品名】(2R)-3-[[tert-butyl(diphenyl)silyl]oxy]-2-methylpropyl 4-methylbenzenesulfonate 【CA登记号】 |
【 分 子 式 】C27H34O4SSi 【 分 子 量 】482.71606 【元素组成】C 67.18% H 7.1% O 13.26% S 6.64% Si 5.82% |
合成路线1
该中间体在本合成路线中的序号：(XXX)The chiral sulfone intermediate (XIV) has been obtained as follows: The silylation of 3-hydroxy-2(R)-methylpropionic acid methyl ester (XXVII) as usual gives the silylated ester (XXVIII), which is reduced to the chiral propanol (XXIX). The reaction of (XXIX) with TsCl and pyridine yields the tosylate (XXX), which is condensed with methyl phenyl sulfone (XXXI) by means of n-BuLi in THF to afford the chiral sulfone (XXXII). Desilylation of (XXXII) with TBAF in THF provides the 4-hydroxy-3-methylbutylsulfone (XXXIII), which is finally resilylated with TBDMS-Cl and imidazole to furnish the target intermediate (XIV).
| 【1】 Mulzer, J.; Ohler, E.; Mantoulidis, A. (Schering AG); Method for producing epothilone B and derivs., and intermediate products for this method. WO 0023452 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XIV) | 40825 | tert-butyl(dimethyl)[[(2S)-2-methyl-4-(phenylsulfonyl)butyl]oxy]silane; (3S)-4-[[tert-butyl(dimethyl)silyl]oxy]-3-methylbutyl phenyl sulfone | C17H30O3SSi | 详情 | 详情 | |
| (XXVII) | 14965 | methyl 3-hydroxy-2-methylpropanoate; METHYL (S)-(+)-3-HYDROXY-2-METHYLPROPIONATE | 80657-57-4 | C5H10O3 | 详情 | 详情 |
| (XXVIII) | 40838 | methyl (2R)-3-[[tert-butyl(diphenyl)silyl]oxy]-2-methylpropanoate | C21H28O3Si | 详情 | 详情 | |
| (XXIX) | 40839 | (2S)-3-[[tert-butyl(diphenyl)silyl]oxy]-2-methyl-1-propanol | C20H28O2Si | 详情 | 详情 | |
| (XXX) | 40840 | (2R)-3-[[tert-butyl(diphenyl)silyl]oxy]-2-methylpropyl 4-methylbenzenesulfonate | C27H34O4SSi | 详情 | 详情 | |
| (XXXI) | 23622 | methyl phenyl sulfone; methyl(dioxo)phenyl-lambda(6)-sulfane | 3112-85-4 | C7H8O2S | 详情 | 详情 |
| (XXXII) | 40841 | (3S)-4-[[tert-butyl(diphenyl)silyl]oxy]-3-methylbutyl phenyl sulfone; tert-butyl[[(2S)-2-methyl-4-(phenylsulfonyl)butyl]oxy]diphenylsilane | C27H34O3SSi | 详情 | 详情 | |
| (XXXIII) | 40842 | (2S)-2-methyl-4-(phenylsulfonyl)-1-butanol | C11H16O3S | 详情 | 详情 |