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Trifluoromethylation of sugar 1,4-lactones Synthesis of 5-deoxy-5,5-5-trifluoro-D and L-ribose and lyxose derivatives


, : Trifluoromethylation of sugar 1,4-lactones Synthesis of 5-deoxy-5,5-5-trifluoro-D and L-ribose and lyxose derivatives. Tetrahedron Letters 34(51): 8241-8244

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 30–40 % overall yield. The key step was a stereoselective reduction of 1,1,1-trifluoro-2-ketoses with LiAlH4 or NaBH4 at an anomeric centre.

US$19.90

DOI: 10.1016/s0040-4039(00)61400-4


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