New Stereospecific Rearrangements of Pyranosides

Abstract Methyl β-D-arabinopyranoside (1), phenyl 1-thio-β-D-galactopyranoside (3), methyl β-L-fucopyranoside (7), methyl β-L-fucopyranoside (9), 1,6-anhydro-β-D-galactopyranoside (D-galactosan; 11), and 1,6-anhydro-β-D-mannopyranoside (D-mannosan; 14) were stereospecifically converted in moderate up to good yields into methyl 4-O-cyclohexylcarbamoyl-2,3-O-(2,2,2-trichloroethylidene)-β-D-lyxopyranoside (2), phenyl 4-(9-cyclohexyIcarbamoyl-6-O-formyl-2,3-O-(2,2,2-trichloroethylidene)-1-thio-β-D-gulopyranoside (4) / phenyl 4-O-cyclohexylcarbamoyl-2,3-O-(2,2,2-trichloroethylidene)-1-thio-β-D-gulopyraoside (5), methyl 4-O-cyclohexylcarbamoyl-2,3-O-(2,2,2-trichloroethylidene)-6-deoxy-α-L-gulopyranoside (8), methyl 2,3-O-(2,2,2-trichloroethylidene)-4-O-cyclohexylcarbamoyl-6-deoxy-β-L-gulopyranoside (10), 1,6-anhydro-4-O-cyclohexyl-carbamoyl-2,3-O-(2,2,2-trichloroethylidene)-β-D-gulopyranoside (12), and 1,6-anhydro-2-O-cyclohexylcarbamoyl-3,4-O-(2,2,2-trichloroethylidene)-β-D-altropyranoside (15), respectively, ...