Neighboring-group participation by C-2 ether functions in glycosylations directed by nitrile solvents

Chin Sheng Chao, Ching Yu Lin, Shaheen Mulani, Wei Cheng Hung, Kwok-Kong Mong*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

55 Scopus citations

Abstract

Ether-protecting functions at C-2 hydroxy groups have been found to play participating roles in glycosylations when the reactions are conducted in nitrile solvent mixtures. The participation mechanism is based on intramolecular interaction between the lone electron pair of the oxygen atom of the C-2 ether function and the nitrile molecule when they are positioned in a cis configuration. A 1,2-cis glycosyl oxazolinium intermediate is formed. This participation, in conjunction with the anomeric effect of the glycosyl donor, confers high 1,2-trans selectivities on glycosylations. Further application of this concept has led to efficient preparations of α-(1→5)-arabinan oligomers.

Original languageEnglish
Pages (from-to)12193-12202
Number of pages10
JournalChemistry - A European Journal
Volume17
Issue number43
DOIs
StatePublished - 17 Oct 2011

Keywords

  • arabinans
  • glycosylation
  • neighboring-group effects
  • nitrile solvents
  • oligosaccharides

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