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Synthesis 1996; 1996(11): 1309-1312
DOI: 10.1055/s-1996-4377
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Highly Diastereoselective Synthesis of Anomeric β-O-Glycopyranosyl Carbamates from Isocyanates

Ruben G. G. Leenders, Rob Ruytenbeek, Eric W. P. Damen, Hans W. Scheeren*
  • *Department of Organic Chemistry, NSR-Center for Molecular Structure Design and Synthesis, University of Nijmegen, Toernooiveld, NL-6525 ED Nijmegen, The Netherlands, Fax +31(24)3652929
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Publication History

Publication Date:
31 December 2000 (online)

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1-β-O-Glycopyranosyl carbamates are prepared with practically 100% β-diastereoselectivity from anomerically unprotected glycopyranosides and isocyanates. The isocyanates are prepared in situ from carboxylic acids via acyl azides.

1-β-O-glycopyranosyl carbamates - isocyanates - Curtius rearrangement - β-diastereoselectivity - prodrug preparation

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