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Some novel nucleophilic displacement reactions in the carbohydrate area and N.M.R. studies of their products Miller, Diane Claudia

Abstract

1,2:5,6-Di-O-isopropylidene-α-D-allofuranose 1, 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 2, and 1,2:3,4-di-O-isopropyli-dene-α-D-galactopyranose 3 have been treated separately in pyridine solution with trifluoromethanesulfonic anhydride, 2,2,2-trifluoroethanesulfonyl chloride, and pentafluorobenzenesulfonyl chloride. Both 1 and 2 afforded the anticipated sulfonic esters. Although 3 also gave the 2,2,2-trifluoroethanesulfonic and pentafluorobenzenesulfonic esters, the reaction with trifluoromethanesulfonic anhydride yielded 6-deoxy-1,2:3,4-di-O-isopropylidene-6-pyridino-α-D-galactopyranose trifluoromethanesulfonate 7. In a second part to this work triphenyltin lithium was separately reacted with each of 1,2:3,4-di-O-methylene-α-D-glucofuranose 22, methyl 2,3-anhydro-4,6-O-benzylidene-α-D-allopyranoside 23 and methyl 2,3-anhydro-4,6-O-benzylidene-a-D-mannopyranoside 24 to form, in every case, a sugar-stannane derivative having a stable carbon-tin bond. N.m.r. studies of both the fluorinated sugar sulfonates and, particularly, of the organotin sugars are also reported.

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