Reaction of acetyl hypofluorite with pyranoid and furanoid glycals

✍ Scribed by Karl Dax; Brigitte I. Glänzer; Gerhard Schulz; Hermann Vyplel

• Book ID: 102992351
• Publisher: Elsevier Science
• Year: 1987
• Tongue: English
• Weight: 513 KB
• Volume: 162
• Category: Article
• ISSN: 0008-6215
• DOI: 10.1016/0008-6215(87)80196-9

✦ Synopsis

The regiospecific syn-addition of acetyl hypofluorite to glycals derived from pentopyranoses led to mixtures of stereoisomers. Stereospecific reactions occurred with furanoid glycals, the direction of addition being governed by the nature of the substituent at C-3. Whereas a benzyloxy group caused attack from the opposite, less-hindered face of the double bond, a hydroxyl group induced addition from the same side. From these reactions, 2-deoxy-2-fluoro derivatives of /?-D-arabino-, a-~ribo-, p-D-lyxo-, and a-D-xylo-pyranose as well as pD-manno-, (Y-D-gluco-, cr-Dribo-, and P-D-arabino-furanose were obtained; their 'H-, 13C-, and lgF-n.m.r. data are given.