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Double Stereodifferentiation in Carbohydrate Coupling Reactions: The Mismatched Interaction of Donor and Acceptor as an Unprecedented Factor Governing the α/β Ratio of Glycoside Formation
Author(s) -
Spijker Nynke M.,
van Boeckel Constant A. A.
Publication year - 1991
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199101801
Subject(s) - disaccharide , glycosylation , acceptor , chemistry , glycosyl , glycosyl donor , glycoside , stereochemistry , enantiomer , carbohydrate , coupling reaction , computational chemistry , organic chemistry , catalysis , biochemistry , physics , condensed matter physics
Two enantiomeric glycosyl donors 1 and 2 were coupled to the glycosyl acceptor 3 under the same conditions. The first case leads to a disaccharide with an α/β ratio of 2/1, the second to a ratio of 1/8.4. This and other experiments show that the stereochemical outcome of glycosylation can be strongly influenced by unfavorable interactions (the formation of matched and mismatched pairs) between glycosyl donor and acceptor.