C-DAUNOSAMINYL DERIVATIVES BY THE WITTIG REACTION

Article abstract of DOI:10.1016/S0008-6215(00)80669-2

C-Glycosylation of a 2-deoxypyranose has been achieved for the first time by conversion of 4-O-p-nitrobenzoyl-N-trifluoroacetyldaunosamine in a Wittig reaction into the corresponding derivative of ethyl 2-(daunosaminyl)acetate.The product was predominantly (54percent) in the desired α-L configuration (separated from the β-L anomer, 15percent) required for further elaboration of C-daunosaminyl derivatives.Conversion into the corresponding derivatives of 2-(α-L-daunosaminyl)acetaldehyde and 2-(α-L-daunosaminyl)ethanol was also achieved.