✦ LIBER ✦
Stereo- and regio-selectivity of diethylaminosulfur trifluoride as a fluorinating reagent for methyl glycosides
✍ Scribed by Chandrasiri W. Somawardhana; Eric G. Brunngraber
- Publisher
- Elsevier Science
- Year
- 1983
- Tongue
- English
- Weight
- 572 KB
- Volume
- 121
- Category
- Article
- ISSN
- 0008-6215
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✦ Synopsis
Methyl gfycopyranosides reacted with dicthylamin~sulfur trifluoride (DAST) in the absence of solvent to yield methyl dideoxy-difluoro and deoxy-fluoro glycopyranosides. Methyl n-D-glycopyranosides produced 6-deoxy-6-fluoro-and 4,6-dideoxy-4,6-ditluoro derivatives with Walden inversion at C-4. Methyl P-D-ghlcopyranoside also produced a 3,6-dideoxy-3,6-difluoro derivative, with Walden inversion at C-3. Methyl 6-~-trityl-~-D-glucopyranoside. reacted with DAST to yield the corresponding 4-deoxy-4-fluorogalactopyranoside derivative.