Further stereoselective reductions of 3-O-hexofuranosyl S-methyl dithiocarbonates with tributyltin deuteride. A comment on mechanism
- 1 January 1980
- journal article
- research article
- Published by CSIRO Publishing in Australian Journal of Chemistry
- Vol. 33 (11) , 2509-2515
- https://doi.org/10.1071/ch9802509
Abstract
The reduction of 1,2:5,6-di-O-isopropylidene-3-O- (methylthio)thiocarbonyl-β-D-altrose, -mannose and -(3-2H)mannose with tributyltin deuteride and hydride leads to highly stereoselective syntheses of 3-deoxy-1,2:5,6-di-O-isopropylidene-β-D-(3-2H)altrose and -(3-2H)mannose. In addition, the reduction of a pair of diastereomeric dithiocarbonates with virtually no stereochemical constraints leads to the same diastereomeric mixture of reduced products, indicating a common radical intermediate for the reduction.Keywords
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