Sulfenate esters as glycosyl acceptors: A novel approach to O-glycosides from thioglycosides and sulfenate esters

✍ Scribed by Yukishige Ito; Tomaya Ogawa

• Publisher: Elsevier Science
• Year: 1987
• Tongue: French
• Weight: 265 KB
• Volume: 28
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)96602-4

✦ Synopsis

The reactions of thioglycosides and sulfenate esters were effected in the presence of Lewis acid to give corresponding 0-glycosides.

The stereoselectivity was highly dependent on the solvent.

Recently

we reported a conceptually novel approach to the synthesis of 2-deoxyglycosides based on the Lewis acid mediated activation of sulfenate esters 1 readily obtainable from R'OSPh X (Lewis ecld) _ R'+OSPh l L -l-r R'O -x-X-1 2 OR \ ,O.