Abstract
2-Arylthio-β-C-D-glucopyranosides with a carbonyl or methoxy group in the lateral chain (1 and 2) can be converted to the corresponding 2-deoxy-β-C-D-glucopyranosides (1a and 2a) using Raney Ni. Reduction of 2-arylthio-β-C-D-glucopyranosides bearing an ester, methoxy, C≡N, or C=C moiety in the side chain (3–6) using n-Bu3SnH in the presence of azobisisobutyronitrile (AIBN) provided the corresponding 2-deoxy-β-C-D-glucopyranosides (3a–6a) without reducing additional functional groups. The application of n-Bu3SnH and AIBN in reaction with 2-arylthio-β-C-D-glucopyranoside (7) containing a Me3Si group bonded to the carbonyl fragment (7) resulted in the reduction of both the 2-ArS and C=O groups.
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ACKNOWLEDGMENT
The authors gratefully acknowledge the University of North Dakota for financial support.