A simple stereoselective synthesis of biologically important 2-halo-2,3-dideoxy-arabinose derivatives from 1,1,1,2-tetrafluoroethane (134a) and 1-chloro-2,2,2-trifluoroethane (133a)

A simple stereoselective three step synthesis of 2-fluoro- and 2-chloro-2,3 -dideoxy arabinose derivatives from the readily available starting material s, (R)-glycidol and either 1,1,1,2-tetrafluoroethane (134a) or 1-chloro-2,2 ,2-trifluroethane (133a), is described. This compares very favourably with the multistep syntheses previously described in the literature. A mechanist ic interpretation of the reaction via an unfavourable 5-endo-trig cyclisati on is given. (C) 2000 Elsevier Science S.A. All rights reserved.