Stereoselective synthesis of β-glycosyl esters of cis-cinnamic acid and its derivatives using unprotected glycosyl donors

Kazumasa Matsuo, Keisuke Nishikawa, Mitsuru Shindo

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

The β-glycosyl esters of cis-cinnamic acid were synthesized directly using Hannesian's unprotected glycosyl donor and the carboxylic acid in toluene. This protocol does not require protecting groups on the glycosyl donors, and high stereoselectivity was achieved. The first synthesis of a potent allelochemical, 1-O-cis-cinnamoyl-β-d-glucopyranose, is also described.

Original languageEnglish
Pages (from-to)5688-5692
Number of pages5
JournalTetrahedron Letters
Volume52
Issue number43
DOIs
Publication statusPublished - Oct 26 2011

Fingerprint

NSC 153174
Stereoselectivity
Pheromones
Toluene
Carboxylic Acids
Esters
Derivatives
cinnamic acid

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Stereoselective synthesis of β-glycosyl esters of cis-cinnamic acid and its derivatives using unprotected glycosyl donors. / Matsuo, Kazumasa; Nishikawa, Keisuke; Shindo, Mitsuru.

In: Tetrahedron Letters, Vol. 52, No. 43, 26.10.2011, p. 5688-5692.

Research output: Contribution to journalArticle

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