文献类型：期刊文献

英文题名：Synthesis of L-glycero- and D-glycero-D-manno-Heptose Building Blocks for Stereoselective Assembly of the Lipopolysaccharide Core Trisaccharide of Vibrio parahemolyticus O2

作者：Wang, Junchang[1];Rong, Jingjing[1];Lou, Qixin[1];Zhu, Yirong[1];Yang, You[1]

机构：[1]East China Univ Sci & Technol, Sch Pharm, Shanghai Key Lab New Drug Design, Shanghai 200237, Peoples R China

年份：2020

卷号：22

期号：20

起止页码：8018

外文期刊名：ORGANIC LETTERS

收录：;WOS:【SCI-EXPANDED(收录号:WOS:000607469900045)】；

基金：Financial support from the National Natural Science Foundation of China (21871081 and 22071054) and the Fundamental Research Funds for the Central Universities (50321031916002 and 22221818014) is gratefully acknowledged.

语种：英文

摘要：Synthesis of bacterial cell surface L-glycero-D-manno-heptose (L,D-Hep)- and D-glycero-D-manno-heptose (D,D-Hep)containing higher carbon sugars is a challenging task. Here, we report a convenient and efficient approach for the synthesis of the L,D-Hep and D,D-Hep building blocks. Using L-lyxose and D-ribose as starting materials, this approach features diastereoselective Mukaiyama-type aldol reactions as the key steps. On the basis of the synthetic L,D-Hep and D,D-Hep building blocks, we achieved the first stereoselective synthesis of the unique alpha-L,D-Hep-(1.3)-alpha-D,D-Hep-(1 5)-alpha-Kdo core trisaccharide of the lipopolysaccharide of Vibrio parahemolyticus O2.