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【结 构 式】 
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【分子编号】37950 【品名】tert-butyl(dimethyl)silyl [4-(tributylstannyl)-1,3-thiazol-2-yl]methyl ether; 2-([[tert-butyl(dimethyl)silyl]oxy]methyl)-4-(tributylstannyl)-1,3-thiazole 【CA登记号】 |
【 分 子 式 】C22H45NOSSiSn 【 分 子 量 】518.46694 【元素组成】C 50.97% H 8.75% N 2.7% O 3.09% S 6.18% Si 5.42% Sn 22.9% |
合成路线1
该中间体在本合成路线中的序号：(V)Lithiation of 2,4-dibromothiazole (I) with n-BuLi at -78 C, followed by condensation with dimethylformamide gave aldehyde (II), which was reduced to alcohol (III) with NaBH4. After protection of the alcohol (III) as the tert-butyldimethylsilyl ether (IV), a second metalation with n-BuLi, and subsequent quenching with tri-n-butyltin chloride furnished stannane (V). Further desilylation of (V) by means of tetrabutylammonium fluoride yielded 2-(hydroxymethyl)-4-(tri-n-butylstannyl)thiazole (VI).
| 【1】 Nicolaou, K.C.; et al.; Total synthesis of epothilone E and analogs with modified side chains through the Stille coupling reaction. Angew Chem. Int Ed Engl 1998, 37, 1-2, 84. |
| 【2】 Nicolaou, K.C.; et al.; Total synthesis of epothilone E and related side-chain modified analogues via a stille coupling based strategy. Bioorg Med Chem 1999, 7, 5, 665. |
| 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) | 37946 | 2,4-dibromo-1,3-thiazole | C3HBr2NS | 详情 | 详情 | |
| (II) | 37947 | 4-bromo-1,3-thiazole-2-carbaldehyde | C4H2BrNOS | 详情 | 详情 | |
| (III) | 37948 | (4-bromo-1,3-thiazol-2-yl)methanol | C4H4BrNOS | 详情 | 详情 | |
| (IV) | 37949 | (4-bromo-1,3-thiazol-2-yl)methyl tert-butyl(dimethyl)silyl ether; 4-bromo-2-([[tert-butyl(dimethyl)silyl]oxy]methyl)-1,3-thiazole | C10H18BrNOSSi | 详情 | 详情 | |
| (V) | 37950 | tert-butyl(dimethyl)silyl [4-(tributylstannyl)-1,3-thiazol-2-yl]methyl ether; 2-([[tert-butyl(dimethyl)silyl]oxy]methyl)-4-(tributylstannyl)-1,3-thiazole | C22H45NOSSiSn | 详情 | 详情 | |
| (VI) | 37951 | [4-(tributylstannyl)-1,3-thiazol-2-yl]methanol | C16H31NOSSn | 详情 | 详情 |