R. Ferrier, J. Hurford
Dec 1, 1974
Citations
0
Influential Citations
7
Citations
Journal
Carbohydrate Research
Abstract
Abstract Reaction of four esters of α- L -arabinofuranosyl bromide with 1,5-diazabicyclo-[5.4.0]undec-5-ene causes elimination of hydrogen bromide. In the case of the tris-(p-nitrobenzoate), only degradation products were observed, but from the other three esters, 1,4-anhydro- L -erythro-pent-1-enitol compounds were isolated. These compounds isomerise readily on standing in non-hydroxylic solvents to give 3-deoxypent-2-enofuranoses, and simultaneously lose benzoic acid to give furans. In ethanolic solution, both the 1,4-anhydropent-1-enitol esters and their 3-deoxy-2-enofuranose isomers react at room temperature to give anomeric mixtures of ethyl 3-deoxypent-2-enofuranosides. Compounds in this series are judged to be too reactive to serve generally as satisfactory glycosylating agents.