ChemInform Abstract: 1,2-cis-C-Glycoside Synthesis by Samarium Diiodide-Promoted Radical Cyclizations.

✍ Scribed by T. SKRYDSTRUP; D. MAZEAS; M. ELMOUCHIR; G. DOISNEAU; C. RICHE; A. CHIARONI; J.-M. BEAU

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 33 KB
• Volume: 28
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199748248

✦ Synopsis

1,2-cis-C-Glycoside Synthesis by Samarium Diiodide-Promoted Radical Cyclizations.

-Glucosyl pyridyl sulfones bearing a silicon-tethered unsaturated group at the C-2 OH position are quickly reduced by SmI2 in the absence of a cosolvent leading to the stereospecific synthesis of 1,2-cis-Cglycosides such as (II), (IV), and (VI). In contrast to glycosyl phenyl sulfones and other aryl sulfones the pyridyl derivatives react more quickly and give optimal yields. This procedure has certain advantages over the corresponding tin hydride method in that it avoids the use of toxic reagents. An application of this radical cyclization strategy is demonstrated by the synthesis of the C-disaccharide (IX). -(SKRYDSTRUP, T.;