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Synthesis of Sugar Azido or Amino Esters and Their Use as Building Blocks for the Preparation of Saccharide Nucleosides
Author(s) -
Xie Juan
Publication year - 2002
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200210)2002:20<3411::aid-ejoc3411>3.0.co;2-q
Subject(s) - chemistry , glycosylation , sugar , glycoside , organic chemistry , protecting group , primary (astronomy) , amino sugar , carbohydrate chemistry , combinatorial chemistry , stereochemistry , biochemistry , alkyl , physics , astronomy
Several sugar azido or amino esters bearing an α‐ or a β‐ C ‐ D ‐glucopyranosyl backbone have been prepared by TMSOTf/Ac 2 O‐mediated α‐ C ‐glycosylation with concurrent selective removal of the primary benzyl group or selective acetolysis of the primary benzyl group of β‐ C ‐glycoside as key steps. Such structures have been successfully used as scaffolds for the synthesis of novel saccharide nucleosides. (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)