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Synlett 1990; 1990(11): 694-696
DOI: 10.1055/s-1990-21214
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Nitriles as Solvents in Glycosylation Reactions: Highly Selective β-Glycoside Synthesis1

Richard R. Schmidt* , Michael Behrendt, Alexander Toepfer
  • *Fakultät Chemie, Universität Konstanz, D-7750 Konstanz, Germany
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Publication Date:
08 March 2002 (online)

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Treatment of glycosyl trichloroacetimidates in nitriles as solvent at low temperatures with trimethylsilyl trifluoro-methanesulfonate (SN1-type conditions) leads under α-face attack to fast nitrilium-nitrile conjugate formation. These intermediates are converted rapidly in the presence of various acceptors into β-disaccharides in high yields and diastereoselectivities.

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