Regioselective glycosylation method using partially protected arabino- and galactofuranosyl thioglycosides as key glycosylating substrates and its application to one-pot synthesis of oligofuranoses.

J Org Chem

Key Laboratory of Drug Targeting, Ministry of Education, and Department of Chemistry of Medicinal Natural Products, West China School of Pharmacy, Sichuan University, Chengdu 610041, People's Republic of China.

Published: April 2012

We describe in this paper the development of a novel regioselective furanosylation methodology using partially protected furanosyl thioglycosides as central glycosylating building blocks and its application in the efficient one-pot synthesis of a series of linear and branched-type arabino- and galactofuranoside fragments structurally related to the cell wall polysaccharides of Mycobacterium tuberculosis , Streptococcus pneumoniae serostype 35A, and sugar beet.

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Source
http://dx.doi.org/10.1021/jo300084gDOI Listing

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