Synthesis of CH2-linked α(2,3)sialylgalactose analogue: On the stereoselectivity of the key Ireland-Claisen rearrangement

Toru Watanabe, Go Hirai, Marie Kato, Daisuke Hashizume, Taeko Miyagi, Mikiko Sodeoka

Research output: Contribution to journalArticle

27 Citations (Scopus)

Abstract

(Chemical Equation Presented) A CH2-linked α(2,3) sialylgalactose analogue was efficiently synthesized using an Ireland-Claisen rearrangement, which was developed recently by our group for constructing a CF2-sialoside. The reaction conditions of the rearrangement were optimized for α-stereoselective formation of the CH2-sialoside. On the basis of the observed temperature effects, the origin of the stereoselectivity of the Ireland-Claisen rearrangement is discussed. Moreover, reconstruction of the 2α-hydroxyl group on the galactose unit of the rearrangement product was achieved by means of stereoselective dihydroxylation and deoxygenation.

Original languageEnglish
Pages (from-to)4167-4170
Number of pages4
JournalOrganic letters
Volume10
Issue number19
DOIs
Publication statusPublished - Dec 1 2008
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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