志贺氏菌 9 型 O 抗原四糖重复单元的汇聚合成。
Convergent synthesis of the tetrasaccharide repeating unit of the O-antigen of Shigella boydii type 9.
机构信息
Bose Institute, Division of Molecular Medicine, P-1/12, C.I.T. Scheme VII-M, Kolkata-700054, India;
出版信息
Beilstein J Org Chem. 2011;7:1182-8. doi: 10.3762/bjoc.7.137. Epub 2011 Aug 29.
Abstract
A convenient synthesis of the tetrasaccharide repeating unit of the O-antigen of Shigella boydii type 9 has been achieved in excellent yield using a [2 + 2] block glycosylation strategy. TEMPO-mediated selective oxidation of the primary alcohol of the tetrasaccharide derivative 8 to the carboxylic group followed by deprotection of the functional groups furnished target tetrasaccharide 1 as its 4-methoxyphenyl glycoside in high yield.
摘要
采用[2+2] 分段糖基化策略，以优异的收率实现了志贺氏菌 9 型 O-抗原四糖重复单元的方便合成。四糖衍生物 8 的伯醇经 TEMPO 介导的选择性氧化为羧酸，然后脱保护基，得到目标四糖 1，以 4-甲氧基苯基糖苷高产率。
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