title: Synthesis of 1,2-cis-2-C-branched aryl-C-glucosides via desulfurization of carbohydrate based hemithioacetals.
abstract: 1-C and 2-C-branched carbohydrates are present as substructures in a number of biologically important compounds. Although the synthesis of such carbohydrate derivatives is extensively studied, the synthesis of 1,2-cis-2-C-branched C-, S-, and N-glycosides is less explored. In this article a synthetic strategy for the synthesis of 1,2-cis-2-C-branched-aryl-C-glucosides is reported via a hydrogenolytic desulfurization of suitably orientated carbohydrate based hemithioacetals. 1,2-cis-2-Hydroxymethyl and 2-carbaldehyde of aryl-C-glucosides have been synthesized using the current strategy in very good yields. The 2-carbaldehyde-aryl-C-glucosides have been identified as suitable substrates for the stereospecific preparation of 2,3-unsaturated-aryl-C-glycosides (Ferrier products).
authors.affiliation: Department of Chemistry, University of Johannesburg, PO Box 524, Auckland Park 2006, South Africa.
authors.forename: Henok H
authors.initials: HH
authors.lastname: Kinfe
authors.affiliation: Department of Chemistry, University of Johannesburg, PO Box 524, Auckland Park 2006, South Africa.
authors.forename: Fanuel M
authors.initials: FM
authors.lastname: Mebrahtu
authors.affiliation: Department of Chemistry, University of Johannesburg, PO Box 524, Auckland Park 2006, South Africa.
authors.forename: Mandlenkosi M
authors.initials: MM
authors.lastname: Manana
authors.affiliation: Department of Chemistry, University of Johannesburg, PO Box 524, Auckland Park 2006, South Africa.
authors.forename: Kagiso
authors.initials: K
authors.lastname: Madumo
authors.affiliation: Department of Chemistry, University of Johannesburg, PO Box 524, Auckland Park 2006, South Africa.
authors.forename: Mokela S
authors.initials: MS
authors.lastname: Sokamisa
keywords: Ferrier product; aryl-C-glucoside; desulfurization; hemithioacetal