Highly efficient stereospecific preparation of Tn and TF building blocks using thioglycosyl donors and the Ph2SO/Tf2O promotor system

David Cato, Therese Buskas, Geert Jan Boons*

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

Abstract

The activation of 2-azido-2-deoxy Tn and TF thioglycosyl donors by the powerful thiophilic promoter system Ph2SO/Tf2O has been investigated. Glycosylation of an Fmoc-protected threonine derivative gave 1,2-cis glycosides in high yields and excellent stereoselectivities. The galactosylation of phenyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D- galactopyranoside was achieved in high yield and without orthoester formation using a trichloroacetimidate donor carrying a 2-O-(2,5-difluorobenzoyl) group. The anomeric thiophenyl group of the constructed TF disaccharide could directly be activated by the van Boom promotor for the glycosylation of a threonine derivative.

Original languageEnglish
Pages (from-to)503-516
Number of pages14
JournalJournal of Carbohydrate Chemistry
Volume24
Issue number4-6
DOIs
Publication statusPublished - 28 Nov 2005
Externally publishedYes

Keywords

  • Glycopeptide
  • Glycosylation
  • TF antigen
  • Thioglycoside
  • Tn antigen

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