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Glycoconjugate Journal

, Volume 29, Issue 5–6, pp 453–456 | Cite as

Facile TMSOTf-catalyzed preparation of 2-deoxy α-O-aryl-D-glycosides from glycosyl acetates

  • Guofang Yang
  • Qingbing Wang
  • Xiaosheng Luo
  • Jianbo Zhang
  • Jie Tang
Article

Abstract

2-Deoxy α-O-aryl glycosides were conveniently obtained by reaction of 2-deoxy-glycosyl acetates with phenols in the presence of TMSOTf as the promoter. The current method provides the O-aryl glycosides with good to excellent yields, and sole alpha selectivity.

Keywords

Stereoselective 2-deoxy sugars Aryl glycoside Glycosyl acetates TMSOTf 

Notes

Acknowledgement

We thank the analytic center of East China Normal University for data measurement. We appreciate Mr Jie Fu for helpful discussion. The project was supported by Shanghai Rising-Star Program (06QA14018) and the Natural Science Foundation of Shanghai (11ZR1410400) and large instruments Open Foundation of East China Normal University (2011–76 & 2012–9).

Supplementary material

10719_2012_9429_MOESM1_ESM.pdf (3.4 mb)
ESM 1 (PDF 3433 kb)

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Copyright information

© Springer Science+Business Media, LLC 2012

Authors and Affiliations

  • Guofang Yang
    • 1
  • Qingbing Wang
    • 1
    • 2
  • Xiaosheng Luo
    • 1
  • Jianbo Zhang
    • 1
  • Jie Tang
    • 1
  1. 1.Department of ChemistryEast China Normal UniversityShanghaiChina
  2. 2.State Key Laboratory of Bioorganic and Natural Products ChemistryShanghai Institute of Organic Chemistry, Chinese Academy of ScienceShanghaiChina

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