3,4-bis(O-tert-butyldimethylsilyl)-6-O-tosyl-D-glucal: A probe for the mechanism of the iodine(III)-promoted allylic oxidation of glycals

✍ Scribed by Kirschning, Andreas

• Book ID: 102368193
• Publisher: John Wiley and Sons
• Year: 1995
• Tongue: English
• Weight: 366 KB
• Volume: 1995
• Category: Article
• ISSN: 0947-3440
• DOI: 10.1002/jlac.1995199511289

✦ Synopsis

Abstract

The reaction of 3,4‐bis(O‐tert‐butyldimethylsilyl)‐6‐O‐tosyl‐D‐glucal 4 with the Koser reagent [PhI(OH)OTs] unexpectedly afforded tetrahydrofurfural 6 as well as 2,3‐anhydropyranose 7 as major products. This unprecedented, stereoselective transformation helps to gain further insight into the mechanism of the well‐documented hypervalent iodine‐promoted allylic oxidation of cyclic enol ethers. A novel chemoenzymatic method for the preparation of glucal 4 in high yield is presented.