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Synthesis of trifluoromethyl analogue of L-fucose and 6-deoxy-D-altrose

1991; Royal Society of Chemistry; Issue: 12 Linguagem: Inglês

10.1039/c39910000796

2050-5639

R. C. Bansal, Barbara Dean, Sen‐itiroh Hakomori, Tatsushi Toyokuni,

Carbohydrate Chemistry and Synthesis

Trifluoromethylation of the acyclic derivative of D-lyxose, 3, with trifluoromethyltrimethylsilane in the presence of tetrabutylammonium fluoride yielded a mixture of trifluoromethyl adducts, 5a and b, which was converted to 6,6,6-trifluoro-L-fucose 9a and 6-deoxy-6,6,6-trifluoro-D-altrose 9bvia selective oxidation of the primary hydroxy group involving treatment of the trimethylsiloxy derivatives, 7a and b, with Collins reagent.