Synthesis of 1,2-cis-2-C-branched aryl-C-glucosides via desulfurization of carbohydrate based hemithioacetals

• Henok H. Kinfe,
• Fanuel M. Mebrahtu,
• Mandlenkosi M. Manana,
• Kagiso Madumo and
• Mokela S. Sokamisa

Beilstein J. Org. Chem. 2015, 11, 583–588, doi:10.3762/bjoc.11.64

• stereospecific preparation of 2,3-unsaturated-aryl-C-glycosides (Ferrier products). Keywords: aryl-C-glucoside; desulfurization; Ferrier product; hemithioacetal; Introduction 1-C (C-glycosides) and 2-C-branched carbohydrates are important carbohydrate analogues which have found wide application in

• prepared from thiochroman 1 and we envisioned that a careful desulfurization could provide aryl-C-glucoside 4 with inherent 1,2-cis relationship between the easily transformable 2-C-branch and the aryl group at the C-2 and C-1 positions, respectively. Although detailed studies on the desulfurization of

• found to be stable and its structure was confirmed by X-ray crystal diffraction analysis (Figure 1) [23]. After the successful synthesis and characterization of the hemithioacetal 3a, our initial desulfurization attempt to prepare the 2-C-branched-α-aryl-C-glucoside 4a involved treatment of a solution