ChemInform Abstract: Coupling of Glycal Derived Thioethyl Glycosyl Donors with Glycal Acceptors. An Advance in the Scope of the Glycal Assembly.

✍ Scribed by P. H. SEEBERGER; M. ECKHARDT; C. E. GUTTERIDGE; S. J. DANISHEFSKY

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 44 KB
• Volume: 29
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199809203

✦ Synopsis

Coupling of Glycal Derived Thioethyl Glycosyl Donors with Glycal

Acceptors.

An Advance in the Scope of the Glycal Assembly. -Glycals can be converted into thioethyl glycosyl donors through 1,2anhydrosugar intermediates. Various participating groups in the C-2 position are examined for formation of β-glucosyl, β-galactosyl, and α-mannosyl linkages. Best employed are thioether glycosyl donors carrying a C-2-pivaloyl protecting group. These give in a novel coupling with glycal acceptors under condition D) a number of disaccharides in high yield. This new methodology is applied to the synthesis of the β-(1-4) linked tetrasaccharide (XIII). -(SEEBERGER,