T. Tsuchiya, K. Ajito, S. Umezawa
Mar 1, 1984
Citations
0
Influential Citations
12
Citations
Journal
Carbohydrate Research
Abstract
The behavior of methyl 4,6-O-cyclohexylidene-2-deoxy-2-trifluoroacetamido-3-O-trifluoromethylsulfonyl-α-d-glucopyranoside (6) with several reagents was examined. By reaction of 6 with lithium chloride or sodium iodide in N,N-dimethylformamide, the corresponding 3-chloro-3-deoxy- and 3-deoxy-3-iodo-allopyranosides were readily obtained. Treatment of 6 with sodium benzoate in N,N-dimethylformamide, or sodium methoxide in methanol, gave several products derived from an initially formed 2,3-allo-epimine. The difference in the foregoing reactions is explained on the basis of hydrogen bonding between 2-NHCOCF3 and 1-OMe. Solvolysis of 6 and methyl 6-benzyloxycarbonylamino-2,6-dideoxy-2-trifluoroacetamido-3-O-trifluoromethylsulfonyl-α-d- glucopyranoside (26) in hot (100°) methanol gave ring-contraction products (18, 27) having bicyclic d-xylofuranoside structures.