Stereoselective 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 | Zendy

Bishwa Raj Bhetuwal | Zendy; Fenglang Wu | Zendy; Shuai Meng | Zendy; Jianglong Zhu | Zendy

Open Access

Stereoselective 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,

Shuai Meng,

Jianglong Zhu

Publication year - 2020

Publication title -

the 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 , tetrasaccharide , trifluoromethanesulfonate , stereoselectivity , alkylation , stereochemistry , electrophile , micrococcus luteus , organic chemistry , catalysis , polysaccharide , biochemistry , escherichia coli , 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).

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