Reduction of 2-Arylthio-β-C-D-Glucopyranosides with Different Functional Groups in the Lateral Chain

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.

Keywords:

• 2-Arylthio-β-C-d-glucopyranosides
• 2-deoxy-β-C-d-glucopyranosides
• β-C-d-glucopyranosides
• Raney Ni
• tributyltin hydride

ACKNOWLEDGMENT

The authors gratefully acknowledge the University of North Dakota for financial support.