title: Some observations on the reductive ring opening of 4,6-O-benzylidene acetals of hexopyranosides with the borane trimethylamine-aluminium chloride reagent.
abstract: Reductive ring openings of 3-O-benzoyl-4,6-O-benzylidene-D-glucopyranosides with BH(3)·NMe(3)-AlCl(3) are accompanied by side reactions, such as debenzoylation and reduction of the benzoate to benzyl ether. This phenomenon was rationalized by aluminium chelate formation between the O-4 acetal and the benzoyl carbonyl group oxygens. It was also shown that these side reactions can be eliminated by using BH(3)·THF as the reducing agent.
authors: Department of Carbohydrate Chemistry, Chemical Research Center, Hungarian Academy of Sciences, Pusztaszeri út 59-67, H-1025 Budapest, Hungary.
authors: Katalin
authors: K
authors: Daragics
authors: Pál
authors: P
authors: Szabó
authors: Péter
authors: P
authors: Fügedi