Wang Qinghui, Zhang Shufen, Yang Jinzong
State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116012, PR China.
Carbohydr Res. 2007 Dec 10;342(17):2657-63. doi: 10.1016/j.carres.2007.08.014. Epub 2007 Aug 28.
Regioselective formation of 6-O-acylsucroses and 6,3'-di-O-acylsucroses in one pot with good yields was achieved for the first time by a typical acylation method of sucrose via its dibutylstannylene acetal. Pure monoesters at OH-6 and diesters at OH-6,3' obtained by these procedures were readily isolated by simple column chromatography, thus overcoming the main difficulties associated with regioselectivity, efficiency, and isolation techniques for the practical preparation. Explanations for the regioselectivities observed during this stannylene acetal-mediated reaction were also proposed based on the structures of the stannylene acetal in solution and the intramolecular migration of stannylenes.
首次通过蔗糖二丁基亚锡缩醛的典型酰化方法，以良好的产率在一锅反应中实现了6-O-酰基蔗糖和6,3'-二-O-酰基蔗糖的区域选择性形成。通过这些方法获得的OH-6位的纯单酯和OH-6,3'位的二酯可通过简单的柱色谱法轻松分离，从而克服了实际制备中与区域选择性、效率和分离技术相关的主要困难。还基于溶液中二丁基亚锡缩醛的结构和亚锡的分子内迁移，对该亚锡缩醛介导的反应过程中观察到的区域选择性进行了解释。
