A Solution to Chemical Pseudaminylation via a Bimodal Glycosyl Donor for Highly Stereocontrolled α- And β-Glycosylation

Research output: Contribution to journal/Conference contribution in journal/Contribution to newspaperJournal articleResearchpeer-review

  • Ruohan Wei, University of Hong Kong
  • ,
  • Han Liu
  • Arthur H. Tang, Sydney University, Sydney
  • ,
  • Richard J. Payne, Sydney University, Sydney
  • ,
  • Xuechen Li, University of Hong Kong

A robust methodology for the stereocontrolled chemical glycosylation of pseudaminic acid has been developed to afford both α- (axial) and β- (equatorial) glycosides reliably with complete stereoselectivity, using a common glycosyl donor (7N-Cbz/5N-azido Pse thioglycoside) simply by changing the reaction conditions. In the CH 2 Cl 2 /MeCN cosolvent, highly β-selective pseudaminylation was observed, while addition of 5.0 equiv DMF in CH 2 Cl 2 gave the α-pseudaminosides.

Original languageEnglish
JournalOrganic Letters
Volume21
Issue10
Pages (from-to)3584-3588
Number of pages5
ISSN1523-7060
DOIs
Publication statusPublished - 2019
Externally publishedYes

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