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有机化学
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有机化学 ›› 1998, Vol. 18 ›› Issue (4): 324-327. 上一篇    下一篇

研究论文

相转移催化法合成1-O-酰基-四-O-乙酰基-β-D-吡喃己糖

赵生敏;潘鑫复;张功成;李洪启;谭干祖   

  1. 中国科学院兰州化学物理研究所;兰州大学化学系
  • 发布日期:1998-08-25

Phase transfer catalyzed synthesis of 1-O-acyl-tetra-O-acetyl-β-D-glucopyranoses and gatactopyranoses

ZHAO SHENGMIN;PAN XINFU;ZHANG GONGCHENG;LI HONGQI;TAN GANZU   

  • Published:1998-08-25

被引次数

60

以氯化三乙基苄基铵作为相转移催化剂, 用2, 3, 4, 6-四-O-乙酰基-β-D-溴代吡喃葡萄糖和2, 3, 4, 6-四-O-乙酰基-β-D-溴代吡喃半乳糖与羧酸反应, 合成了相应的1-O-酰基-2, 3, 4, 6-四-O-乙酰基-β-D-吡喃葡萄糖和半乳糖。通过解析这些化合物的^1H NMR和红外光谱, 确证其糖甙键构型为β。该相转移催化法具有反应条件温和, 后处理简单和立体选择性强等优点。

关键词: 己糖, 相转移催化剂, 铵, 氯化铵 P, 羧酸, 有机合成, 半乳糖, 吡喃糖, 相转移催化, 吡喃糖

1-O-Acyl-2, 3, 4, 6-tetra-O-acetyl-β-D-glucopyranoses and 1-O-acyl-2, 3, 4, 6-tetra-O-acetyl-β-D-gatactopyranoses were synthesized by reaction of 2, 3, 4, 6-tetra-O-acetyl-α -D-glucopyranosyl bromide and 2, 3, 4, 6-tetra-O-acetyl-α -D-gatactopyranosyl bromide with carboxylic acid, using trienthy benzyl ammonium chloride as phase-transfer catalyst. The method has advantages of mild reaction conditions, easy separation of products and high stereospecificity.

Key words: HEXOSE, AMMONIUM, PHASE TRANSFER CATALYST, PYRANOSE, AMMONIUM CHLORIDE P, GALACTOSE, ORGANIC SYNTHESIS, PYRANOSE, PHASE TRANSFER CATALYSIS, CARBOXYLIC ACID

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