Stereoselective Reduction of 3-O-Hexofuranosyl S-Methyl Dithiocarbonates with Tributyltin Deuteride
- 1 January 1979
- journal article
- Published by CSIRO Publishing in Australian Journal of Chemistry
- Vol. 32 (2)
- https://doi.org/10.1071/ch9790411
Abstract
The reduction of several 3-O-hexofuranosyl (gluco, allo, galacto, gulo) S-methyl dithiocarbonates with tributyltin deuteride leads to highly stereoselective syntheses of 3-deoxy-[3-2H]hexofuranoses.Correspondingly, the reduction of the 3-O-[3-2H]hexofuranosyl (allo, gulo) S-methyl dithiocarbonates with tributyltin hydride leads to the epimeric (C3) 3-deoxy-[3-2H]hexofuranoses, and the reduction with tributyltin deuteride leads to the 3-deoxy-[3,3-2H2]hexofuranose.Keywords
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