Chemical Synthesis of beta-Homonojirimycin, of Its N-Butyl Derivative, and of "Methyl Homoazacellobioside"
beta-Homonojirimycin (2) was prepared by the highly stereoselective double reductive amination of a 2,6-heptodiulose derivative (6 or 13) using ammonium formate and NaBH(3)CN. The process was unsuccessful with primary amines. The synthesis of N-butyl-beta-homonojirimycin (19) was achieved by the N-butanoylation of a derivative of 2 followed by the reduction of the resulting tertiary amide. Compound 19 was found to be completely devoid of anti-HIV activity, in marked contrast with N-butyl-1-deoxynojirimycin. The coupling of the 1-O-p-toluenesulfonyl derivative of 2, compound 20, with methyl 2,3,6-tri-O-benzyl-alpha-D-glucopyranoside, followed by a deprotection step, provided pseudodisaccharide 23, the "homoaza" analog of methyl alpha-cellobioside and a potential inhibitor of beta-glucan-processing enzymes.
Saavedra
Oscar M.
OM
Department of Chemistry, State University of New York, P.O. Box 6016, Binghamton, New York 13902-6016.
Martin
Olivier R.
OR