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Palladium‐Catalyzed Improved Regio‐ and Stereoselective O‐Glycosylation of D ‐Glucal‐Derived β‐ and α‐Vinyl Oxiranes
Author(s) -
Reddy Y. Suman,
Lahiri Rima,
Vankar Yashwant D.
Publication year - 2012
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.201200242
Subject(s) - glucal , chemistry , stereoselectivity , glycosylation , glycosyl , glycal , glycosyl donor , catalysis , palladium , glycoside , anomer , chemoselectivity , organic chemistry , stereochemistry , biochemistry
A Pd 0 ‐catalyzed glycosylation of D ‐glucal‐derived vinyloxiranes as excellent glycosyl donors has been accomplished in a regio‐ and stereoselective manner. Various glycosyl acceptors upon reaction with vinyl oxiranes 1a and 1b produced the corresponding 2,3‐unsaturated O ‐glycosides in good to excellent yields within five minutes. The above reaction has also been utilized in the synthesis of 2,3‐unsaturated trisaccharides, which are potential precursors of fully oxygenated, deoxy and dideoxy sugars.