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

Kiyomi Ohba, Yuichi Koga, Sumihiro Nomura, Masaya Nakata

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)1007-1010
Number of pages4
JournalTetrahedron Letters
Volume56
Issue number8
DOIs
Publication statusPublished - 2015 Feb 18

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Lactones
Esters
C-glycoside

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Functionalized aryl-β-C-glycoside synthesis by Barbier-type reaction using 2,4,6-triisopropylphenyllithium. / Ohba, Kiyomi; Koga, Yuichi; Nomura, Sumihiro; Nakata, Masaya.

In: Tetrahedron Letters, Vol. 56, No. 8, 18.02.2015, p. 1007-1010.

Research output: Contribution to journalArticle

Ohba, Kiyomi ; Koga, Yuichi ; Nomura, Sumihiro ; Nakata, Masaya. / Functionalized aryl-β-C-glycoside synthesis by Barbier-type reaction using 2,4,6-triisopropylphenyllithium. In: Tetrahedron Letters. 2015 ; Vol. 56, No. 8. pp. 1007-1010.
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AU - Nakata, Masaya

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