4.4 Article

Indium salts-catalyzed O and S-glycosylation of bromo sugar with benzyl glycolate: an unprecedented hydrogenolysis

Journal

TETRAHEDRON LETTERS
Volume 57, Issue 13, Pages 1425-1429

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2016.02.039

Keywords

Glycosylation; beta-Glycosides; Thio-glycosides; Hydrogenolysis; Indium tribromide

Funding

  1. Kleberg Foundation
  2. HHMI program

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Various O and S-glycosyl esters and their corresponding acids are synthesized through a reaction of bromo sugar and benzyl glycolate in the presence of indium trichloride and indium tribromide as promoter. We discovered unprecedented catalytic effects of indium tribromide in glycosylation and hydrogenolysis in a one-pot operation. The sugar acid is a potential chiral auxiliary for the synthesis of biologically active compounds of diverse interests. Published by Elsevier Ltd.

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