CARB 71 |
| Cyanogenic glycoside (R)-2,3,4,6-tetra-O-acetyl-(b)-D-glucopyranosyl-mandelonitrle was successfully synthesized from 2,3,4,6-tetra-O-acetyl-1-O-1,3,2-dioxaphosphacyclohexane-(a,b)-D-glucopyranosyl-2-oxide and the cyanohydrin chiral mandelonitrile in a yield of 72%. The use of 1,3-diylphosphate activation of the glucose ring for the glycosylation reaction allowing the desired b-glycoside provides an alternative means for the synthesis of these cyanogenic glycosides. This methodology of 1,3-diylphosphates will be applied to the synthesis of the natural product amygdalin I, a cyanogenic digylcoside. The preparation of these compounds will enable investigation of their anti-feeding properties to be undertaken.
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General Posters
6:00 PM-8:00 PM, Tuesday, August 21, 2007 BCEC -- Exhibit Hall - B2, Poster
Division of Carbohydrate Chemistry |
