Journal
CARBOHYDRATE RESEARCH
Volume 346, Issue 1, Pages 7-15Publisher
ELSEVIER SCI LTD
DOI: 10.1016/j.carres.2010.11.002
Keywords
Arabinofuranose; 1,2,5-Orthobenzoate; Ring opening; Thioglycosides; Building blocks
Funding
- Russian Foundation for Basic Research [07-03-00830]
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beta-D-Arabinofuranose 1,2,5-orthobenzoates with 3-O-acetyl, 3-O-benzoyl, and 3-O-chloroacetyl groups were prepared in an efficient manner starting from readily available crystalline methyl 2,3,5-tri-O-benzoyl-alpha-D-arabinofuranoside, and ring-opening reactions of these compounds with O- and S-nucleophiles were studied. Optimized conditions leading to the formation of the respective monosaccharide adducts (up to 96% isolated yields) and to alpha-(1 -> 5)-linked disaccharide thioglycosides with 5'-OH unprotected (up to 30% isolated yields) were found. Basing on these results, a novel approach for effective differentiation of 3,5-diol system and 2-hydroxy group in arabinofuranose thioglycosides was proposed. The selectively protected derivatives prepared are valuable building blocks for the assembly of linear and branched oligoarabinofuranosides. (C) 2010 Elsevier Ltd. All rights reserved.
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