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【结 构 式】 
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【分子编号】49637 【品名】tert-butyl[[(2R)-6-isopropoxy-3,6-dihydro-2H-pyran-2-yl]methoxy]diphenylsilane; tert-butyl(diphenyl)silyl [(2R)-6-isopropoxy-3,6-dihydro-2H-pyran-2-yl]methyl ether 【CA登记号】 |
【 分 子 式 】C25H34O3Si 【 分 子 量 】410.62866 【元素组成】C 73.13% H 8.35% O 11.69% Si 6.84% |
合成路线1
该中间体在本合成路线中的序号：(III)The synthesis of dihydropyrancarbaldehyde intermediate (V) has been performed as follows: The oxidation of the selenium derivative (I) with H2O2 followed by in situ elimination gives the dihydropyranone (II), which is reduced with DIBAL to the corresponding lactol and protected as the isopropyl ether (III) by means of PPTS and isopropanol. The deprotection of the silyl ether of (III) with TBAF affords the carbinol (IV), which is finally oxidized with TPAP and NMO to provide the desired carbaldehyde intermediate (V).
| 【1】 Boger, D.L.; et al.; Total synthesis of fostriecin (CI-920). J Am Chem Soc 2001, 123, 18, 4161. |
| 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) | 49635 | (6R)-6-([[tert-butyl(diphenyl)silyl]oxy]methyl)-3-(phenylselanyl)tetrahydro-2H-pyran-2-one | C28H32O3SeSi | 详情 | 详情 | |
| (II) | 49636 | (6R)-6-([[tert-butyl(diphenyl)silyl]oxy]methyl)-5,6-dihydro-2H-pyran-2-one | C22H26O3Si | 详情 | 详情 | |
| (III) | 49637 | tert-butyl[[(2R)-6-isopropoxy-3,6-dihydro-2H-pyran-2-yl]methoxy]diphenylsilane; tert-butyl(diphenyl)silyl [(2R)-6-isopropoxy-3,6-dihydro-2H-pyran-2-yl]methyl ether | C25H34O3Si | 详情 | 详情 | |
| (IV) | 49638 | [(2R)-6-isopropoxy-3,6-dihydro-2H-pyran-2-yl]methanol | C9H16O3 | 详情 | 详情 | |
| (V) | 49639 | (2R)-6-isopropoxy-3,6-dihydro-2H-pyran-2-carbaldehyde | C9H14O3 | 详情 | 详情 |