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.Full text not available in this repository. (Request a copy from the Strathclyde author)
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.
|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|
|Depositing user:||Pure Administrator|
|Date Deposited:||26 Mar 2012 12:49|
|Last modified:||26 Aug 2016 02:11|