高等学校化学学报 ›› 1992, Vol. 13 ›› Issue (9): 1212.

• 论文 • 上一篇    下一篇

蔗糖分子中羟基的选择性保护的研究

吴虹桥, 李翠娟, 王世玉   

  1. 北京大学化学系, 100871
  • 收稿日期:1991-09-09 出版日期:1992-09-24 发布日期:1992-09-24
  • 通讯作者: 王世玉

Studies on the Selectively Protecting Groups of Hydroxyls in Sucrose

WU Hong-Qiao, LI Cui-Juan, WANG Shi-Yu   

  1. Department of Chemistry, Peking University, Beijing, 100871
  • Received:1991-09-09 Online:1992-09-24 Published:1992-09-24

摘要: 蔗糖和原乙酸三烷基酯反应后,经三苯甲基化、乙酰化以及乙酰基由4-位到6-位的基团迁移反应,选择性地保护了蔗糖分子中的羟基基团,合成了一系列蔗糖乙酸酯.4,6-原乙酸蔗糖六乙酸酯在酸催化下水解和醇解,相应地得到2,3,6,1',3',4',6'-七-O-乙酰基蔗糖和2,3,1',3',4',6'-六-O-乙酰基蔗糖。这些都是合成蔗糖衍生物方便的中间体,在糖化学的研究中得到应用.

关键词: 蔗糖乙酸酯, 原乙酸三烷基酯, 4, 6-原乙酸蔗糖六乙酸酯

Abstract: Reaction of sucrose with trialkyl orthoacetate,subsequent tritylation,acetylation,and detritylation afforded derivatives of sucrose acetate by selectively blocking specific hydroxyls in sucrose and 4-6 acetyl migration.The treatment of sucrose alkyl 4,6-orthoacetate hexaaeetate with water or alcohol in the presence of an acid catalyst afforded corresponding 2,3,6,1',3',4',6'-hepta-O-acetylsucrose and 2,3.1',3',4',6'-hexa-O-acetylsucrose.These derivatives of sucrose acetate were available from sucrochemical studies and have been developed as convenient intermediate for the synthesis of sucrose derivatives.

Key words: Sucrose acetate, Trialkyl orthoacetate, Sucrose aikyl 4,6-orthoacetate hexaacetate

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