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【结 构 式】

【分子编号】47251

【品名】(4S,4aR,7aR,8R)-4-[[tert-butyl(dimethyl)silyl]oxy]-8-(3,4-dimethoxyphenyl)-7-oxo-4,4a,5,7,7a,8-hexahydrofuro[2,3-f][2]benzofuran-4-carbonitrile

【CA登记号】

【 分 子 式 】C25H31NO6Si

【 分 子 量 】469.60978

【元素组成】C 63.94% H 6.65% N 2.98% O 20.44% Si 5.98%

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:(VII)

Reaction of 3-furancarboxaldehyde (I) with potassium cyanide in the presence of tert-butyldimethylsilyl chloride and ZnI2 gave the O-silylated cyanohydrin (II). Addition of 2(5H)-furanone (III) to the lithium anion of (II), followed by addition of 3,4-dimethoxybenzaldehyde (V) to the intermediate (IV), yielded adduct (VI). Subsequent acid cyclization of (VI) by means of trifluoroacetic acid or methanesulfonic acid provided the tricyclic derivative (VII) as a diastereomeric mixture. Desilylation of (VII) with concomitant cyanide elimination using either tetrabutylammonium fluoride at low temperature or aqueous ammonium fluoride gave rise to ketone (VIII). This was then epimerized to the title compound by treatment with triethylamine in boiling toluene. Alternatively, desilylation of (VII) with tetrabutylammonium fluoride at room temperature provided directly the title diastereoisomer.

1 Iwasaki, T.; Sugiura, M.; Matsuoka, Y.; Matsumoto, M.; Kitamura, K. (Tanabe Seiyaku Co., Ltd.); Biphenyl derivs.. EP 0386778; JP 1990235884; US 5066669 .
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) 47247 3-Furaldehyde 498-60-2 C5H4O2 详情 详情
(II) 47248 2-[[tert-butyl(dimethyl)silyl]oxy]-2-(3-furyl)acetonitrile C12H19NO2Si 详情 详情
(III) 19267 2(5H)-furanone;furan-2(5H)-one;2-Buten-1,4-olide 497-23-4 C4H4O2 详情 详情
(IV) 47249   C16H22LiNO4Si 详情 详情
(V) 18304 3,4-Dimethoxybenzaldehyde; Veratraldehyde 120-14-9 C9H10O3 详情 详情
(VI) 47250 2-[[tert-butyl(dimethyl)silyl]oxy]-2-[4-[(3,4-dimethoxyphenyl)(hydroxy)methyl]-5-oxotetrahydro-3-furanyl]-2-(3-furyl)acetonitrile C25H33NO7Si 详情 详情
(VII) 47251 (4S,4aR,7aR,8R)-4-[[tert-butyl(dimethyl)silyl]oxy]-8-(3,4-dimethoxyphenyl)-7-oxo-4,4a,5,7,7a,8-hexahydrofuro[2,3-f][2]benzofuran-4-carbonitrile C25H31NO6Si 详情 详情
(VIII) 47252 (4R,4aR,7aR,8R)-4-[[tert-butyl(dimethyl)silyl]oxy]-8-(3,4-dimethoxyphenyl)-7-oxo-4,4a,5,7,7a,8-hexahydrofuro[2,3-f][2]benzofuran-4-carbonitrile C25H31NO6Si 详情 详情
(IX) 47253 (4aR,7aR,8R)-8-(3,4-dimethoxyphenyl)-4a,5,7a,8-tetrahydrofuro[2,3-f][2]benzofuran-4,7-dione C18H16O6 详情 详情
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