4.5 Article

Synthesis of novel 2-deoxy-β-benzyl-C-glycosides by highly stereo- and chemoselective hydrogenation of exo-glycals

Journal

CARBOHYDRATE RESEARCH
Volume 393, Issue -, Pages 23-25

Publisher

ELSEVIER SCI LTD
DOI: 10.1016/j.carres.2014.04.009

Keywords

Wittig reaction; exo-Glycals; Hydrogenation; Palladium catalyst; C-Glycosides

Funding

  1. Comision de Investigaciones Cientificas de la Provincia de Buenos Aires (CICPBA)
  2. UNLP
  3. CONICET

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Novel 2-deoxy-beta-benzyl-C-glycosides were prepared in good yields and excellent stereoselectivity by a route involving the Wittig reaction of glycosyl phosphonium salts and reduction of exo-glycals as key steps. Hydrogenation of benzyl protected enol ethers was performed with Pd/C(en) as an effective chemoselective catalyst to afford exclusively beta anomers. (C) 2014 Elsevier Ltd. All rights reserved.

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