Yoshitake Naoi

Stereoselectivities in the coupling reaction between silytated pyrimidine bases and 1-halo-2,3-dideoxyribose

Coupling reactions between 1-chloro-2,3-dideoxyribose and silylated pyrimidines have been examined from the point of stereoselectivity. When the reaction was carried out in chloroform, the selectivity was in the anomeric ratio of α:β=4:6. On the other hand, the presence of tertiary amine raises the selectivity to α:β=3:7

The synthesis of 2'-deoxy-5-trifluoromethyluridine utilizing a coupling reaction

The coupling reaction between 1-α-chloro-2-deoxyribose derivative and silylated 5-trifluoromethyluracil was examined. The best stereoselectivity was obtained when the reaction was carried out using a large amount of silylated base in the presence of anhydrous zinc chloride