Glycosylations Directed by the Armed-Disarmed Effect with Acceptors Containing a Single Ester Group

Thomas Højsholm Schmidt, Robert Madsen

Research output: Contribution to journalJournal articlepeer-review

Abstract

A selective glycosylation reaction controlled by the armed-disarmed effect is described by the use of phenyl thioglycosides. The donor thioglycoside is fully protected with benzyl ethers while the acceptor thioglycoside contains benzyl ethers at position 2 and 3 and a strongly electron-withdrawing pentafluorobenzoate ester group at position 6. The coupling can be performed with galactose, glucose, manose, and phthalimide-protected glucosamine to afford the corresonding 1,4-linked disaccharides in good yield. These disaccharides can act as glycosyl donors for an additional coupling reaction in the same pot if another acceptor and more promoter are added. In this way, two consecutive glycosylations can be achieved to afford trisaccharides in one operation.
Original languageEnglish
JournalEuropean Journal of Organic Chemistry
Issue number23
Pages (from-to)3935-3941
ISSN1434-193X
DOIs
Publication statusPublished - 2007

Keywords

  • Carbohydrates
  • Glycosylation
  • Protecting groups
  • Tandem reactions
  • Armed-disarmed effect

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