Synthesis and intramolecular glycosylation of sialyl mono-esters of o-xylylene glycol. The importance of donor configuration and nitrogen protecting groups on cyclization yield and selectivity; isolation and characterization of a N-sialyl acetamide indicative of participation by acetonitrile

被引：10

作者：

Amarasekara, Harsha ^{[1
]}

Crich, David ^{[1
]}

机构：

[1] Wayne State Univ, Dept Chem, Detroit, MI 48202 USA

来源：

CARBOHYDRATE RESEARCH | 2016年 / 435卷

基金：

美国国家科学基金会; 美国国家卫生研究院;

关键词：

N-Glycosyl amide; Lactonization; Sialic acid; Spirodiolide; Thioglycoside; Ritter reaction; CATION CLOCK REACTIONS; STEREOSELECTIVE-SYNTHESIS; ACETYLNEURAMINIC ACID; (3,3)-SIGMATROPIC REARRANGEMENT; ANOMERIC CONFIGURATION; GANGLIOSIDE; GLYCOSIDES; ANALOGS; FACILE; C-13;

D O I：

10.1016/j.carres.2016.09.019

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The synthesis and cyclization reactions, leading to spirocyclic medium ring-sized diolides, of o-(hydroxymethyl)xylylene monoesters of sialyl thioglycosides is described. Cyclization yields and stereoselectivities are found to vary as a function of the anomeric stereochemistry of the thioglycoside and of the N5 protecting group, and these effects are discussed in terms of the reaction mechanism. Cyclization in the presence of acetonitrile results in the isolation and characterization of a Ritter-type N-sialyl acetamide, which affords strong evidence for the participation of acetonitrile in the form of sialyl nitrilium ions. (C) 2016 Elsevier Ltd. All rights reserved.

引用

页码：113 / 120

页数：8

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