Open AccessStereoselective Synthesis of 2-Azido-2-deoxy-β-d -mannosides via Cs2CO3-Mediated Anomeric O-Alkylation with Primary Triflates: Synthesis of a Tetrasaccharide Fragment of Micrococcus luteus Teichuronic Acid
Author(s) -
Bishwa Raj Bhetuwal,
Fenglang Wu,
Sheng Meng,
Jianglong Zhu
Publication year - 2020
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.0c02370
Subject(s) - chemistry , anomer , trifluoromethanesulfonate , alkylation , tetrasaccharide , stereochemistry , stereoselectivity , micrococcus luteus , electrophile , chemical synthesis , organic chemistry , catalysis , biochemistry , polysaccharide , escherichia coli , in vitro , gene
Cesium carbonate-mediated anomeric O-alkylation of various protected 2-azido-2-deoxy-d-mannoses with primary triflate electrophiles afforded corresponding 2-azido-2-deoxy-β-mannosides in good yields and excellent anomeric selectivity. In addition, 1,3-dibromo-5,5-dimethylhydantoin was found to be the optimal oxidant for preparation of those 2-azido-2-deoxy-d-mannoses from their corresponding thioglycosides. The utilization of this method was demonstrated in the synthesis of a tetrasaccharide fragment of Micrococcus luteus teichuronic acid containing N -acetyl-β-d-mannosaminuronic acid (ManNAcA).