Unusually Stable Picoloyl-Protected Trimethylsilyl Glycosides for Nonsymmetrical 1,1′-Glycosylation and Synthesis of 1,1′-Disaccharides with Diverse Configurations

Yen Chu Luke Lu, Bhaswati Ghosh, Kwok-Kong Mong*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

10 Scopus citations

Abstract

Nonsymmetrical 1,1′-disaccharides and related derivatives constitute structural components in various glycolipids and natural products. Some of these compounds have been shown to exhibit appealing biological properties. We report a direct yet stereoselective 1,1′-glycosylation strategy for the synthesis of nonsymmetrical 1,1′-disaccharides with diverse configurations and sugar components. The strategy is based on the joined forces of a new class of configurationally stable glycoside acceptors and stereodirecting thioglycoside donors. The new glycoside acceptors feature a picoloyl (Pico) protecting group at the remote C4/C3 position that confers unusual stability on TMS glycosides under acidic conditions.

Original languageEnglish
Pages (from-to)6905-6918
Number of pages14
JournalChemistry - A European Journal
Volume23
Issue number28
DOIs
StatePublished - 1 Jan 2017

Keywords

  • carbohydrates
  • donor–acceptor systems
  • glycosides
  • glycosylation
  • protecting groups

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