Journal of the Chemical Society. Perkin transactions I p. 1183 - 1186 (1988)
Update date:2022-08-10
Topics:
Kenne, Lennart
Unger, Per
Wehler, Thomas
The methyl α-glycosides of 4-amino-4,6-dideoxy-D-mannopyranose (perosamine), N-acylated with either formic, acetic, or (S)-2,4-dihydroxybutanoic acid, have been synthesized.The (1)H and (13)C n.m.r. spectra of these substances and the parent, non-N-acylated glycoside, demonstrated how the chemical shifts are influenced by the N-acylation.The N-formyl derivative occured in two conformations, s-cis and s-trans, and the free-energy barrier between these, 86.9 kJ mol-1, was defined by dynamic n.m.r. spectroscopy.
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