Expeditious synthesis of C-glycosyl conjugated dienes and aldehydes from sugar lactones

Wen Bin Yang, Chuan Fa Chang, Shwu Huey Wang, Chin Fen Teo, Chun Hung Lin

Research output: Contribution to journalArticle

28 Citations (Scopus)

Abstract

Several C-glycosyl conjugated dienes were prepared in two steps from protected sugar lactones via addition of allylmagnesium chloride and the subsequent dehydration. A sequence of allylic addition, ozonolysis and dehydration led to the corresponding glycosyl conjugated aldehydes. These conjugated functionalities can be used as diagnostic chromophores for sugar synthesis and purification. The synthetic studies of glycosyl dienes were also pursued. Hydroboration of a sugar diene led to either homoallylic alcohol or spiroacetal depending on the workup conditions.

Original languageEnglish
Pages (from-to)4657-4660
Number of pages4
JournalTetrahedron Letters
Volume42
Issue number28
DOIs
Publication statusPublished - 2001 Jul 9

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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