Functionalized aryl-β-C-glycoside synthesis by Barbier-type reaction using 2,4,6-triisopropylphenyllithium

 

Kiyomi Ohba, Yuichi Koga, Sumihiro Nomura, and Masaya Nakata

“Functionalized aryl-β-C-glycoside synthesis by Barbier-type reaction using 2,4,6-triisopropylphenyllithium”
Tetrahedron Letters, 2015, 56, 1007–1010.

http://www.sciencedirect.com/science/article/pii/S0040403915000696

We developed an efficient synthetic route for functionalized aryl-β-C-glycosides, which are difficult to prepare by conventional methods. An aryl halide having an ester, cyano, or carbonyl group was treated with 2,4,6-triisopropylphenyllithium in the presence of a δ-lactone (Barbier-type reaction conditions) to afford a coupling product. The following deoxygenation gave the desired aryl-β-C-glycoside in good yield.

  • a Medicinal Chemistry Research Laboratories, Mitsubishi Tanabe Pharma Corporation, 1000 Kamoshida-cho, Aoba-ku, Yokohama 227-0033, Japan
  • b Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan

keywords

  • C-Glycoside;
  • Aldonolactone;
  • Barbier-type reaction;
  • Halogen–metal exchange reaction;
  • 2,4,6-Triisopropylphenyllithium

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