Open AccessStereoselective Synthesis of β-d -Manno-heptopyranoside via Cs2CO3-Mediated Anomeric O-Alkylation: Synthesis of a Tetrasaccharide Repeat Unit of Bacillus thermoaerophilus Surface-Layer Glycoprotein
Author(s) -
Sheng Meng,
Ishani Lakshika Hettiarachchi,
Bishwa Raj Bhetuwal,
Prakash Thapa,
Jianglong Zhu
Publication year - 2022
Publication title -
journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.2
H-Index - 228
eISSN - 1520-6904
pISSN - 0022-3263
DOI - 10.1021/acs.joc.2c00168
Subject(s) - tetrasaccharide , stereoselectivity , anomer , alkylation , stereochemistry , total synthesis , chemistry , organic chemistry , catalysis , polysaccharide
Stereoselective synthesis of d-glycero- and l-glycero-β-d-mannoheptosides has been achieved by cesium carbonate-mediated β-selective anomeric O -alkylation of the corresponding d-mannoheptoses. In addition, this method has been utilized in the total synthesis of a tetrasaccharide repeat unit of Bacillus thermoaerophilus surface-layer glycoprotein.