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Synthesis 1988; 1988(9): 694-697
DOI: 10.1055/s-1988-27673
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A Convenient Synthesis of 2-Deoxy-β-D-glucopyranosides

Rainer Preuss* , Richard R. Schmidt
  • *Fakultät Chemie, Universität Konstanz, D-7750 Konstanz, Federal Republic of Germany
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Publication Date:
18 September 2002 (online)

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The O-(2-deoxy-2-phenylthio-α-D-glucopyranosyl) trichloroacetimidate α-3 was obtained from 3,4,6-tri-O-benzyl-D-glucal (1) in a two-step procedure. This compound is a powerful glucopyranosyl donor, which with typical alcohol acceptors provided mainly the corresponding 2-phenylthio-substituted 2-deoxy-β-D-glucopyranosides β-5a to β-5d. These were converted by Raney nickel treatment to the desired 2-deoxy-β-D-glucopyranosides 6 in high yields.