| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 5222555 | Tetrahedron | 2009 | 6 Pages |
Abstract
The preparation of 2-deoxy-2-thiotolylfuranosyl azides and C-glycosides from a 2,3-anhydrosugar thioglycoside with the d-lyxo stereochemistry is described. The reaction is performed by treatment of the thioglycoside with a trimethylsilylated nucleophile in the presence of BF3·OEt2. This approach provides a convenient route to the preparation of the corresponding 2-deoxy-furanosyl azides and C-glycosides. In contrast, the use of an isomeric substrate, with the 2,3-anhydro-d-ribo stereochemistry, gave these products in low to modest yield.
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Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Dianjie Hou, Todd L. Lowary,