A new glycosidation method through nitrite displacement on substituted nitrobenzenes
A new glycosidation method through nitrite displacement on substituted nitrobenzenes
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DOI：
10.1016/j.carres.2006.11.017
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发表时间：
2007-02-26
影响因子：
3.1
通讯作者：
Ziegler, Thomas
中科院分区：
文献类型：
--
作者：
Alvarez-Mico, Xavier;Calvete, Mario J. F.;Ziegler, Thomas
葡萄糖、葡糖胺、半乳糖、甘露糖和乳糖系列中的苄基、苯甲酰基和乙酰基保护的I-OH和1-SH糖与被一个或两个吸电子取代基（如硝基和氰基）活化的硝基苯反应，以50-100%产率得到相应的芳基糖苷。亚硝酸根被1-OH葡萄糖的SNAr置换是可逆的，并且主要产生α-糖苷，而1-SH葡萄糖不发生端基异构化，并且产生β-糖苷。因此，所制备的二氰基苯基糖苷是用于通过模板合成制备酞菁-糖缀合物的有用的结构单元。(c)2006爱思唯尔有限公司保留所有权利。
Benzyl, benzoyl, and acetyl protected I-OH and 1-SH glycoses in the glucose, glucosamine, galactose, mannose, and lactose series react with nitrobenzenes activated by one or two electron withdrawing substituents like nitro and cyano to afford the corresponding aryl glycosides in 50-100% yield. The SNAr displacement of nitrite by 1-OH glycoses is reversible and gives predominantly the alpha-glycosides, whereas 1-SH glycoses do not anomerize and afford the beta-glycosides. Thus, the prepared dicyanophenyl gycosides are useful building blocks for the preparation of phthalocyanine-glycoconjugates via template synthesis. (c) 2006 Elsevier Ltd. All rights reserved.