Synthesis of substituted septanosyl-1,2,3-triazoles.
A carbohydrate-based oxepine, derived from 2-deoxy-D-arabino-hexopyranose, was used to prepare a family of septanosyl-1,2,3-triazoles in four steps. DMDO mediated epoxidation of the oxepine followed by trapping of the intermediate 1,2-anhydroseptanose by sodium azide gave the beta-substituted glycosyl azide. The septanosyl azide was then reacted with a number of alkynes under thermal Huisgen or copper(I) mediated reaction conditions. Hydrogenolysis of benzyl protecting groups gave substituted septanosyl-1,2,3-triazoles. The new septanose-based structures were then evaluated as potential glycosidase inhibitors.
Castro
Steve
S
Department of Chemistry, University of Connecticut, U-3060, 55 North Eagleville Road, Storrs, CT 06269, United States.
Cherney
Emily C
EC
Snyder
Nicole L
NL
Peczuh
Mark W
MW
D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D006026:Glycoside Hydrolases / Q000032:analysis / Q000037:antagonists & inhibitors* / Q000145:classification; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry; D010082:Oxepins / Q000737:chemistry; D013056:Spectrophotometry, Ultraviolet; D013696:Temperature; D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
D010082:Oxepins; D014230:Triazoles; D006026:Glycoside Hydrolases; D009584:Nitrogen