Photolabile Protecting Group-Mediated Synthesis of 2-Deoxy-Glycosides

Xiaoqian Li, Zhi Ma, Rongkun Liu, Mattan Hurevich, You Yang*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

12 Scopus citations

Abstract

A green and efficient photolabile protecting group (PPG)-mediated glycosidation approach for the synthesis of 2-deoxy-glycosides is reported. By employing ortho-nitrobenzyl carbonate (oNBC) as PPG, N,N-dimethylformamide (DMF)-modulated SPhosAuNTf2-promoted glycosidation with per-oNBC-protected 2-deoxy-glycosyl ynenoates affords the 2-deoxy-glycosides with moderate to excellent α-selectivities presumably depending on the reactivities of the acceptor alcohols. Based on the PPG-mediated glycosidation approach, oligosaccharides with three to six oNBC groups are effectively achieved. The multiple oNBC groups in the 2-deoxy-glycosides are completely cleaved by irradiation at 365 nm, resulting in the desired 2-deoxy-glycosides in an efficient manner without affecting the common alkyne, alkene, azide functional groups and the traditional protecting groups on the aglycones.

Original languageAmerican English
Pages (from-to)3309-3314
Number of pages6
JournalChinese Journal of Chemistry
Volume39
Issue number12
DOIs
StatePublished - Dec 2021

Bibliographical note

Publisher Copyright:
© 2021 SIOC, CAS, Shanghai & WILEY-VCH GmbH

Keywords

  • Glycosides
  • Glycosyl ynenoates
  • Glycosylation
  • Gold
  • Protecting groups

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