Decarboxylative Glycosylation Reaction Intra- Versus Intermolecular Reaction Course

Mixed glycosyl carbonates are transformed under acid catalysis into glycosides. Competition experiments with equal amounts of carbonates 5 and 6 led to complete scrambling of the glycosyl donor and acceptor moieties: not only the expected glycosides 7 and 8 but in practically equal amounts also glyc...

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Bibliographic Details
Published in:Tetrahedron letters 1997-04, Vol.38 (17), p.2943-2946
Main Authors: Scheffler, Götz, Schmidt, Richard R.
Format: Article
Language:English
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Summary:Mixed glycosyl carbonates are transformed under acid catalysis into glycosides. Competition experiments with equal amounts of carbonates 5 and 6 led to complete scrambling of the glycosyl donor and acceptor moieties: not only the expected glycosides 7 and 8 but in practically equal amounts also glycosides 9 and 10 were obtained. Therefore, decarboxylative glycosylation under acid catalysis is an intermolecular reaction; the reaction course is discussed. © 1997 Elsevier Science Ltd.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(97)00561-3