| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 5274913 | Tetrahedron Letters | 2012 | 4 Pages |
Abstract
Septanosyl fluorides, prepared from protected pyranoses, were used as donors in glycosylation reactions. The fluorides were synthesized by the addition of vinyl Grignard to the pyranoses followed by ozonolysis and then DAST-mediated fluorination. Activation in the presence of nucleophiles then provided the product glycosides. High α-stereoselectivity was observed for glycosylations using a donor that had a free C2 hydroxyl group; a model where the hydroxyl group participates to guide the stereochemical outcome is proposed.
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Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Jaideep Saha, Mark W. Peczuh,