title: Reinvestigation of the iodocyclization of 4,5,7-tri-O-benzyl-3-(N-benzylacetamido)-1,2,3-trideoxy-D-gluco-hept-1-enitol: unexpected formation of a 1,3-imino-heptitol derivative.
abstract: The NIS-mediated iodocyclization of 4,5,7-tri-O-benzyl-3-(N-benzylacetamido)-1,2,3-trideoxy-D-gluco-hept-1-enitol gave unexpectedly a 1,3-imino-heptitol derivative, namely 2-O-acetyl-N-benzyl-4,5,7-tri-O-benzyl-1,3-dideoxy-1,3-imino-D-glycero-D-ido-heptitol. This compound is a new example of a rare class of azetidine imino alditol derivatives which have interesting properties such as glycosidase inhibitors. The physical and spectral data for this imino heptitol were essentially identical to those reported for 2,6-anhydro-4,5,7-tri-O-benzyl-3-(N-benzylacetamido)-3-deoxy-D-glycero-D-ido-heptitol, a derivative of C-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)methanol obtained from the same precursor [Lay, L.; Nicotra, F.; Panza, L.; Verani, A. Gazz. Chim. Ital. 1992, 122, 345-348]; these findings cast doubts on the structure reported for the latter product.
authors.affiliation: Department of Chemistry, State University of New York, PO Box 6016, Binghamton, NY 13902-6016, USA.
authors.forename: Adewale
authors.initials: A
authors.lastname: Eniade
authors.forename: Olivier R
authors.initials: OR
authors.lastname: Martin
mesh_terms: D000081:Acetamides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001384:Azetidines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D003500:Cyclization; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D005989:Glycerides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors*; D007455:Iodine / Q000737:chemistry
chemical_list: C457460:2,6-anhydro-4,5,7-tri-O-benzyl-3-(N-benzylacetamido)-3-deoxy-glycero-ido-heptitol; D000081:Acetamides; D001384:Azetidines; D004791:Enzyme Inhibitors; D005989:Glycerides; D007455:Iodine; D006026:Glycoside Hydrolases