4.7 Article

Regioselective Glycosylation Method Using Partially Protected Arabino- and Galactofuranosyl Thioglycosides as Key Glycosylating Substrates and Its Application to One-Pot Synthesis of Oligofuranoses

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 77, Issue 7, Pages 3025-3037

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jo300084g

Keywords

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Funding

  1. NSFC [21172156, 21021001]
  2. National Basic Research Program of China (973 Program) [2010CB833202]
  3. Ministry of Education [NCET-08-0377, 20100181110082]
  4. Sichuan Province of China [08ZQ026-029]

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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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