Syntheses of difluorinated carbasugar phosphates from trifluoroethanol.
Difluorinated cyclohexene diols (prepared from trifluoroethanol) can be elaborated to racemic analogues of phosphorylated sugars via regioselective protection and phosphorylation of the exposed C-1 hydroxyl group. Cis-diol protection was achieved using stannylene methodology, though the regioselectivity depended on the orientation of the methyl group at C-5. UpJohn dihydroxylation is effective with the phosphotriester in place and global deprotection to the tetrol monophosphates is efficient.
Anderl
Timo
T
Department of Chemistry, University of Leicester, University Road, Leicester, LE1 7RH, UK.
Audouard
Christophe
C
Miah
Afjal
A
Percy
Jonathan M
JM
Rinaudo
Giuseppe
G
Singh
Kuldip
K
D054329:Carbasugars / Q000138:chemical synthesis*; D054879:Halogenation; D013403:Sugar Phosphates / Q000138:chemical synthesis*; D014270:Trifluoroethanol / Q000737:chemistry*
D054329:Carbasugars; D013403:Sugar Phosphates; D014270:Trifluoroethanol