Journal
TETRAHEDRON
Volume 68, Issue 52, Pages 10769-10779Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2012.01.078
Keywords
beta-Lactams; Glycosylation; Iodine; Stereospecific; Carbohydrates
Categories
Funding
- Stevens Institute of Technology
- Howard Hughes Medical Institute
- Kleberg Foundation of Texas
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Glycosylation of racemic and optically active alpha-hydroxy beta-lactams by reaction with a few glycal derivatives in the presence of catalytic amounts of iodine has provided stereospecific formation of alpha-glycosides. This method has been extended for the preparation of optically active hydroxy beta-lactams in excellent yields. The stereochemistry and nature of the glycals as well as the stereochemistry of the beta-lactam ring has a profound influence for effective glycosylation. (C) 2012 Elsevier Ltd. All rights reserved.
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