• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【分子编号】62160

【品名】(4aR,8R,8aS)-2-(4-methoxyphenyl)hexahydropyrano[3,2-d][1,3]dioxine-6,8-diol

【CA登记号】

【 分 子 式 】C14H18O6

【 分 子 量 】282.29332

【元素组成】C 59.57% H 6.43% O 34.01%

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:(XXIV)

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
Extended Information