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Synthesis of 4,4-difluoroglycosides using ring-closing metathesis

Percy, J.M. and Audouard, C. and Fawcett, J. and Griffith, G.A. and Pintat, S. and Smith, C.A. (2004) Synthesis of 4,4-difluoroglycosides using ring-closing metathesis. Organic and Biomolecular Chemistry, 2. pp. 528-541.

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Abstract

4-Deoxy-4,4-difluoro-glycosides have been synthesised for the first time via a direct sequence involving ring-closing metathesis and indium-mediated difluoroallylation with 1-bromo-1,1-difluoropropene in water. Two protecting group strategies were explored, one to allow protection of the primary C-6 hydroxyl group throughout the sequence, while the second was intended to allow deprotection after RCM and before dihydroxylation. The benzyl ether could be used in the first role, and pivaloyl is effective in the second. Dihydroxylations were highly stereoselective and controlled by the orientation of the glycosidic C-O bond.

Item type: Article
ID code: 38692
Keywords: ring-closing metathesis , 4-difluoroglycosides , dihydroxylations, Chemistry, Biochemistry, Organic Chemistry, Physical and Theoretical Chemistry
Subjects: Science > Chemistry
Department: Faculty of Science > Pure and Applied Chemistry
Related URLs:
    Depositing user: Pure Administrator
    Date Deposited: 26 Mar 2012 13:49
    Last modified: 04 Sep 2014 19:34
    URI: http://strathprints.strath.ac.uk/id/eprint/38692

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