Exocyclic vinyl ethers of ketofuranosides

Yosi Bechor, Amnon Albeck

Research output: Contribution to journalArticlepeer-review

4 Scopus citations

Abstract

Exocyclic vinyl ether derivatives of sugars are found in biosynthetic pathways and may serve as useful synthetic intermediates. The ketose subfamily of sugars is the least characterized in this field. Thus, the synthesis of exocyclic vinyl ether derivatives of ketohexoses via β-elimination was studied with respect to the nature of the 6-O leaving group and the protection of the 4-hydroxy group. We applied this study to protected l-sorbofuranoside and d-tagatofuranoside sugar derivatives in which the 4-hydroxy group and the 6-O-leaving group are in the syn configuration. Some reactions involving deprotection and reductive rearrangement of the tagatose-derived vinyl ether product were also studied.

Original languageEnglish
Pages (from-to)2080-2089
Number of pages10
JournalTetrahedron
Volume64
Issue number9
DOIs
StatePublished - 25 Feb 2008

Keywords

  • Enol ether
  • Ketose
  • Sugar derivatives
  • β-Elimination

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