Organic chemistry

Trifluoromethanesulfonate

Combinatorial chemistry

Trimethylsilyl

Trimethylsilyl trifluoromethanesulfonate

Reagent

Gene

Catalysis

Product distribution

Chemistry

Acetamide

Ribonucleoside

Biochemistry

Nucleosides and Nucleotides

Combination of bis(trimethylsilyl)acetamide as a silylating reagent and trimethylsilyl trifluoromethanesulfonate as a catalyst forms an exceptionally stable system for a facile one-pot preparation of 6-oxopurine ribonucleosides. The 7β isomer of the ribonucleosides, formed first, is converted into the 9β isomer presumably via the 7,9-diribonucleoside. The procedure affords both 7β and 9β isomers, but finally yields the 9β isomer as the main product.

A Simple One-Pot Method for 6-Oxopurine Ribonucleoside Synthesis: Control and Mechanism of Isomer Distribution