Effective isomerization of 3',5'-O-(tetraisopropyldisiloxane-1,3-diyl) nucleosides in the presence of trimethylsilyl trifluoromethanesulfonate

Abstract

Trimethylsilyl trifluoromethanesulfonate catalyze effective isomerization of 3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)nucleosides (1) in 1,2-dicloroethane at 0°C into 2',3'-O-(tetraisopropyldisiloxane-1,3-diyl)- derivatives (2), which can be obtained in 55-90% yields. On the other hand nucleosides 1 were found to be stable in the presence of tin tetrachloride. Only in the case of uridine derivative 1a a substantial amount of isomerization product 2a was formed. © ARKAT USA, Inc.