三种保护的二糖苯丙素苷的合成研究

Synthesis of Three Protective Phenylpropanoid Glycosides

本文采用先成苷法,从已合成的2-对烯丙氧苯乙基-4,6-O-亚苄基-β-D-葡萄糖苷(1)出发,经2位选择性乙酰化、3位引入三乙酰基保护的鼠李糖基、4,6位脱去亚苄基,得到了关键的中间体4;在化合物4的葡萄糖4、6位分别引入对位取代的肉桂酰基,便得到了保护的二糖苯丙素苷5、7、8。与后成苷法相比,路线缩短一步,收率有所提高。

2 - O - Acetylation of 2 - (4 - allyloxyphenyl) ethyl 4,6 - O - benzylidene - (3 - D -glucopyranoside (-) gave 2, which reacted with triacetylrhamnopyranosyl bromide to yield 3. Protective Osmanthuside B6(5) was synthesized by reaction of p - acetyloxycinnarnoyl chloride and 4 at low temperature, which was obtained by removing benzylidene of 3. Selective acetylation of 4 gave 6. Compound 6 reacted with p - acetyloxycinnarnoyl chloride and 3, 4 - di - O - allylcaffeic acid respectively to afford two corresponding protective disaccharide phenylpropanoid glycosides.7 and 8.