糖脂的克罗顿酯化法：KRN7000 类似物的合成。
The Crotylation Way to Glycosphingolipids: Synthesis of Analogues of KRN7000.
机构信息
Hunter College, The City University of New York (CUNY) , 695 Park Avenue, New York, New York 10021, United States.
The Graduate Center, CUNY , 365 Fifth Avenue, New York, New York 10016, United States.
出版信息
Org Lett. 2016 Sep 16;18(18):4654-7. doi: 10.1021/acs.orglett.6b02284. Epub 2016 Aug 25.
Abstract
A synthesis of glycosphingolipids that centers on the reaction of O- and C-glycosyl crotylstannanes and relatively simple lipid aldehydes is described. The modularity of this strategy and versatility of the crotylation products make this an attractive approach to diverse, highly substituted libraries. The methodology is applied to analogues of the potent imunostimulatory glycolipid KRN7000, including O-, methylene-, and fluoromethine-linked isosteres with diastereomeric ceramide segments and 2-amido substitutes.
摘要
本文描述了一种以 O-和 C-糖基烯丙基锡烷与相对简单的脂醛反应为中心的糖脂的综合方法。该策略的模块化和烯丙基化产物的多功能性使其成为制备多种高度取代文库的一种有吸引力的方法。该方法应用于具有立体异构的神经酰胺片段和 2-酰胺取代基的强效免疫刺激糖脂 KRN7000 的类似物，包括 O-、亚甲基-和氟亚甲基连接的异构体。
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