Synthesis of the pentasaccharide repeating unit corresponding to the capsular polysaccharide of Escherichia coli O20:K83:H26

被引：3

作者：

Shit, Pradip ^{[1
]}

Misra, Anup Kumar ^{[1
]}

机构：

[1] Bose Inst, Div Mol Med, Block EN-80, Salt Lake,Sect V, Kolkata 700091, India

来源：

TETRAHEDRON | 2022年 / 122卷

关键词：

Pentasaccharide; Polysaccharide; E; coli; Glycosylation; Oxidation; HClO4-SiO2; ESCHERICHIA-COLI; BENZYLIDENE ACETAL; GLYCOSYL DONORS; DIARRHEA; EFFICIENT; DERIVATIVES; INFECTIONS; HCLO4-SIO2; CONVERSION; CLEAVAGE;

D O I：

10.1016/j.tet.2022.132948

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A concise synthetic strategy has been developed for the synthesis of the pentasaccharide repeating unit of the capsular polysaccharide of Escherichia coli (E. coli) strain applying block [2 +3] stereoselective glycosylation. A functionalized disaccharide thioglycoside donor prepared using "armed-disarmed " glycosylation concept, was coupled with suitably protected trisaccharide glycosyl acceptor in the presence of a combination of N-iodosuccinimide (NIS) and perchloric acid supported over silica (HClO4-SiO2) to give the target pentasaccharide derivative in 65% yield. A late-stage regioselective oxidation of the primary hydroxyl group using a combination of TEMPO and Bis(acetoxy)iodobenzene (BAIB) furnished D- galacturonic acid moiety in the functionalized pentasaccharide derivative. (C) 2022 Elsevier Ltd. All rights reserved.

引用

页数：6

共 32 条

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