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有机化学
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有机化学 ›› 1997, Vol. 17 ›› Issue (6): 529-534. 上一篇    下一篇

研究论文

三种保护的二糖苯丙素苷的合成研究

张三奇;李中军;王安邦;蔡孟深;冯锐   

  1. 北京医科大学药学院;中国军事医学科学院
  • 发布日期:1997-12-25

Synthesis of three protective phenylpropanoid glycosides

ZHANG SANQI;LI ZHONGJUN;WANG ANBANG;CAI MENGSHEN;FENG RUI   

  • Published:1997-12-25

被引次数

4

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。

关键词: 葡萄糖 P, 糖苷, 二糖, 有机合成, 乙酰化, 鼠李糖

2-O-Acetylation of 2-(4-allyloxyphenyl) ethyl 4,6-O-benzylidene- β-D-glucopyranoside (1) gave 2, which reacted with triacetylrhamnopyranosyl bromide to yield 3. Protective Osmanthuside B~6 (5) was synthesized by reaction of p-acetyloxycinnamoyl 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-acetyloxycinnamoyl chloride and 3,4-di-O-allylcaffeic acid respectively to afford two corresponding protective disaccharide phenylpropanoid glycosides, 7 and 8.

Key words: PYRANE P, ORGANIC SYNTHESIS, DISACCHARIDE, ACETYLATION, RHAMNOSE, GLYCOSIDE

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