Synthesis of Arabinoxylan Oligosaccharides by Pre-Activation-Based Iterative Glycosylations

Emilie Nørmølle Underlin, Maximilian Felix Böhm, Robert Madsen*

*Corresponding author for this work

Research output: Contribution to journalJournal articleResearchpeer-review

127 Downloads (Pure)

Abstract

A concise synthetic strategy has been developed for assembling densely substituted arabinoxylan oligosaccharides, which are valuable substrates for characterizing hemicellulose-degrading enzymes. The xylan backbone has been prepared by an iterative pre-activation-based glycosylation approach with phenyl thioglycosides. The pre-activation has been performed with in situ generated p-nitrobenzenesulfenyl triflate prior to addition of the acceptor. The glycosylation temperature was shown to have an important impact on the yield of the coupling. The arabinose substituents have been introduced in one high-yielding glycosylation with a N-phenyl trifluoroacetimidate donor. The strategy has been successfully employed for the synthesis of three heptasaccharides in seven steps and overall yields of 24 - 36% from the corresponding monosaccharide building blocks.
Original languageEnglish
JournalJournal of organic chemistry
Volume84
Issue number24
Pages (from-to)16036-16054
Number of pages19
ISSN0022-3263
DOIs
Publication statusPublished - 2019

Fingerprint

Dive into the research topics of 'Synthesis of Arabinoxylan Oligosaccharides by Pre-Activation-Based Iterative Glycosylations'. Together they form a unique fingerprint.

Cite this