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

• and 5a’ was treated with a catalytic amount of K2CO3 according to Scheme 3 to afford 2,3-unsaturated-α-aryl-C-glycoside 9a (Ferrier product) which was claimed to have been synthesized under acidic conditions [26] by a completely different reaction protocol. However, our spectroscopic data were not in

• agreement with the reported data [26]. Firstly, the integration of the protons reported in the literature does not correspond to the number of hydrogen atoms present in the Ferrier product 9a; secondly, the aldehydic carbonyl carbon appeared at 200.3 ppm which is off downfield by 10 ppm relative to the

Efficient carbon-Ferrier rearrangement on glycals mediated by ceric ammonium nitrate: Application to the synthesis of 2-deoxy-2-amino-C-glycoside

• Alafia A. Ansari,
• Y. Suman Reddy and
• Yashwant D. Vankar

Beilstein J. Org. Chem. 2014, 10, 300–306, doi:10.3762/bjoc.10.27

• experiments of compound 12. Proposed mechanism. Synthesis of 2-deoxy-2-amino-C-glycoside 12 from Ferrier product 2a. Optimization of reaction conditions. Reaction of glycals with allyltrimethylsilane by using CAN. Reaction of glycals with other nucleophiles. Supporting Information Supporting Information File