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Stereoselectivity of Glycosylation May Change During the Reaction Course: Highly α‐Stereoselective Sialylation Achieved by Supramer Approach
Author(s) -
Koov Leonid O.,
Malysheva Nelly N.,
Orlova Anna V.
Publication year - 2009
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/ejoc.200801017
Subject(s) - stereoselectivity , chemistry , glycosylation , glycosyl , anomer , stereochemistry , supramolecular chemistry , combinatorial chemistry , organic chemistry , catalysis , molecule , biochemistry
The stereoselectivity of NIS/TfOH‐promoted glycosylation with O ‐acetylated N ‐acetylneuraminic acid phenyl thioglycoside was found to be dependent on the reaction time. Highly α‐stereoselective sialylation (27:1 anomer ratio) was achieved by decreasing the reaction time (from 3 h to 15 min) and by adding a non‐reacting compound (1 equiv.) capable of modifying the structure of hydrogen‐bonded supramolecular aggregates (supramers) of the glycosyl donor. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)