CARB 80 |
| Alpha-GlcNAc mercaptan 1 reacts with certain phosphorus(III) and (V) reagents to afford glycomimetic S-glycosylphosphothioates such as 2. Under oxidative conditions, however, an intermediate S-glycosylphosphothioite 3 can give, instead of 2, a rearranged P-glycosylphosphonothioate (4). Preparative, mechanistic, and stereochemical aspects of this radical rearrangement will be presented.
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General Papers: Synthesis of Carbohydrates and Derivatives
1:30 PM-5:10 PM, Wednesday, 29 March 2006 Georgia World Congress Center -- B409, Oral
Division of Carbohydrate Chemistry |
