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Stereoselective Synthesis of α‐Keto‐deoxy‐ D ‐ glycero ‐ D ‐ galacto‐ nonulosonic Acid Glycosides by Means of the 4,5‐ O ‐Carbonate Protecting Group
Author(s) -
Crich David,
Navuluri Chandrasekhar
Publication year - 2010
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200907178
Subject(s) - stereoselectivity , glycoside , group (periodic table) , derivative (finance) , protecting group , chemistry , stereochemistry , organic chemistry , catalysis , business , alkyl , finance
Unrivaled : A 1‐adamantyl thioglycoside derivative of the nonulosonic acid KDN, carrying a 4,5‐ O ‐carbonate protecting group, is a highly efficient and α‐selective KDN donor when activated using N ‐iodosuccinimide (NIS) and trifluoromethanesulfonic acid (TfOH). Glycosylations conducted with this protecting group do not suffer from competing glycal formation.