Trifluoromethylation of Sugar 1,4-Lactones: Synthesis of 5-Deoxy-5,5,5-Trifluoro-D and L-Ribose and Lyxose Derivatives

Article abstract of DOI:10.1016/S0040-4039(00)61400-4

The four 5-deoxy-5,5,5-trifluoro-D and L-ribo and -lyxo furanoses were synthesized from lactones using CF3SiMe3 in 5 or 6 steps and 30-40percent overall yield.The key step was a stereoselective reduction of 1,1,1-trifluoro-2-ketoses with LiAlH4 or NaBH4 a