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【结 构 式】 
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【分子编号】62161 【品名】(4aR,8R,8aS)-8-hydroxy-2-(4-methoxyphenyl)tetrahydropyrano[3,2-d][1,3]dioxin-6(4H)-one 【CA登记号】 |
【 分 子 式 】C14H16O6 【 分 子 量 】280.27744 【元素组成】C 60% H 5.75% O 34.25% |
合成路线1
该中间体在本合成路线中的序号：(XXV)2-Deoxy-D-glucose (XXII) is protected as the cyclic acetal (XXIV) employing p methoxybenzaldehyde dimethyl acetal (XXIII) in the presence of TsOH. Subsequent oxidation of the anomeric hydroxyl group of (XXIV) with Br2 leads to lactone (XXV). After protection of the remaining 3-hydroxyl group of (XXV) as the silyl ether (XXVI), olefination with the Tebbe reagent provides the exocyclic vinyl ether (XXVII). Treatment of (XXVII) with PPTS and MeOH affords a separable mixture of epimeric methylketals (XXVIII). Desilylation of the desired isomer yields alcohol (XXIX), which is then oxidized to ketone (XXX) employing the Dess-Martin periodinane reagent.
| 【1】 Horigome, M.; Motoyoshi, H.; Watanabe, H.; Kitahara, T.; A synthesis of FR901464. Tetrahedron Lett 2001, 42, 46, 8207. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XXII) | 62159 | (4R,5S,6R)-6-(hydroxymethyl)tetrahydro-2H-pyran-2,4,5-triol | C6H12O5 | 详情 | 详情 | |
| (XXIII) | 26485 | 1-(dimethoxymethyl)-4-methoxybenzene | 2186-92-7 | C10H14O3 | 详情 | 详情 |
| (XXIV) | 62160 | (4aR,8R,8aS)-2-(4-methoxyphenyl)hexahydropyrano[3,2-d][1,3]dioxine-6,8-diol | C14H18O6 | 详情 | 详情 | |
| (XXV) | 62161 | (4aR,8R,8aS)-8-hydroxy-2-(4-methoxyphenyl)tetrahydropyrano[3,2-d][1,3]dioxin-6(4H)-one | C14H16O6 | 详情 | 详情 | |
| (XXVI) | 62162 | (4aR,8R,8aR)-8-{[tert-butyl(dimethyl)silyl]oxy}-2-(4-methoxyphenyl)tetrahydropyrano[3,2-d][1,3]dioxin-6(4H)-one | C20H30O6Si | 详情 | 详情 | |
| (XXVII) | 62163 | {[(4aR,8R,8aR)-2-(4-methoxyphenyl)-6-methylenehexahydropyrano[3,2-d][1,3]dioxin-8-yl]oxy}(tert-butyl)dimethylsilane; 4-((4aR,8R,8aR)-8-{[tert-butyl(dimethyl)silyl]oxy}-6-methylenehexahydropyrano[3,2-d][1,3]dioxin-2-yl)phenyl methyl ether | C21H32O5Si | 详情 | 详情 | |
| (XXVIII) | 62164 | 4-((4aR,8R,8aR)-8-{[tert-butyl(dimethyl)silyl]oxy}-6-methoxy-6-methylhexahydropyrano[3,2-d][1,3]dioxin-2-yl)phenyl methyl ether; {[(4aR,8R,8aR)-6-methoxy-2-(4-methoxyphenyl)-6-methylhexahydropyrano[3,2-d][1,3]dioxin-8-yl]oxy}(tert-butyl)dimethylsilane | C22H36O6Si | 详情 | 详情 | |
| (XXIX) | 62165 | (4aR,6S,8R,8aS)-6-methoxy-2-(4-methoxyphenyl)-6-methylhexahydropyrano[3,2-d][1,3]dioxin-8-ol | C16H22O6 | 详情 | 详情 | |
| (XXX) | 62166 | (4aR,6S,8aR)-6-methoxy-2-(4-methoxyphenyl)-6-methyltetrahydropyrano[3,2-d][1,3]dioxin-8(4H)-one | C16H20O6 | 详情 | 详情 |