Direct chemical glycosylation with pentenyl- and thioglycoside donors of N-acetylglucosamine
Direct chemical glycosylation with pentenyl- and thioglycoside donors of N-acetylglucosamine
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DOI：
10.1016/j.carres.2010.02.013
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发表时间：
2010-05-07
影响因子：
3.1
通讯作者：
Jensen, Henrik H.
中科院分区：
文献类型：
--
作者：
Krag, Jonas;Christiansen, Mira S.;Jensen, Henrik H.
研究了n -乙酰氨基葡萄糖（GlcNAc）的戊基和噻吩基糖苷作为糖基供体，在二氯甲烷中由n -碘丁二酰亚胺（NIS）和金属三氟酸盐促进直接制备GlcNAc的o -糖苷。糖基受体1-辛醇和(-)-薄荷醇对两种供体都有很好的糖基化产率，戊基糖苷在产率方面稍好。以碳水化合物为基础的受体与苯基化的glcnac -戊烯基供体反应，但只提供低至中等产量的双糖。结果表明，多种金属三氟酸盐均可作为NIS和中间体恶唑啉的活化剂。(C) 2010 Elsevier Ltd.版权所有。
The use of pentenyl and thiophenyl glycosides of N-acetylglucosamine (GlcNAc) as glycosyl donors for the direct preparation of O-glycosides of GlcNAc promoted by N-iodosuccinimide (NIS) and metal triflates in dichloromethane has been investigated. Both glycosyl acceptors 1-octanol and (-)-menthol resulted in good glycosylation yields for both types of donors with pentenyl glycosides being somewhat superior in terms of yield. Carbohydrate-based acceptors were reacted with a benzylated GlcNAc-pentenyl donor but only provided disaccharides in poor to moderate yields. The results show that a variety of metal triflates are capable of acting as an activator for both NIS and the intermediate oxazoline. (C) 2010 Elsevier Ltd. All rights reserved.