Synthesis of 5-O-benzyl-2-C-β-fluoromethyl-1,2,3-tri-O-acetyl-D- ribofuranose

Abstract

The novel, protected fluoromethylribose (10) was prepared in 7 steps (26% overall yield) from commercially available D-ribonolactone. First, the three hydroxyl groups were protected as the 2,3-isopropylidene-5-benzyl derivative. Reduction of the resulting fully protected ribonolactone to the lactol was achieved by using Cp2TiF2-catalysed hydrosilylation, followed by hydrolysis. Reaction with formaldehyde installed the 2-C-β-hydroxymethyl group. Treatment with DAST gave the 1-fluoro-2-C-β-fluoromethyl derivative, which, on hydrolysis and acetylation, afforded 5-O-benzyl-2-C-β-fluoromethyl-1,2,3-tri-O-acetyl-D- ribofuranose. ©ARKAT.