Synthesis of a carbon analogue of N-acetylmannosamine via acetolysis on a relatively stable ozonide.
After a 2-methylpropenyl group was added to a carbohydrate framework through regioselective opening of a glucose-derived epoxide, hydrolysis or acetolysis of the methyl glycoside in various derivatives was problematic. Ozonolysis of the olefin followed by brief treatment with dimethyl sulfide gave a mixture of diastereomeric ozonides that proved to be stable for weeks at room temperature. Acetolysis of these ozonides at low temperature allowed selective cleavage of the methyl glycoside in the presence of the 1,2,4-trioxolane as well as selective formation of the alpha-acetate.
Chen
Liqiang
L
Department of Chemistry, University of Iowa, Iowa City, Iowa 52242-1294, USA.
Wiemer
David F
DF
D000085:Acetates; D002236:Carbohydrate Conformation; D006595:Hexosamines / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D008958:Models, Molecular; D010126:Ozone
D000085:Acetates; D006595:Hexosamines; D007202:Indicators and Reagents; D010126:Ozone; C002022:N-acetylmannosamine