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Synthesis and characterization of four novel 2-(trimethylsilyl)ethyl glycosides

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Abstract

Four novel 2-(trimethylsilyl)ethyl glycosides have been synthesized by a short and efficient route starting from d-glucose. Their structures were elucidated by applying high-resolution mass spectra, and one-dimensional and two-dimensional NMR techniques. These glycosides were prepared and used as intermediate building blocks in the scheme developed for oligosaccharide construction.

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References

  1. H. Pellissier, Tetrahedron 61, 2947 (2005)

    Article  CAS  Google Scholar 

  2. G. Wulff, G. Röhle, Angew. Chem. Int. Ed. Engl. 13, 157 (1974)

    Article  CAS  Google Scholar 

  3. A. Michael, Am. Chem. J. 1, 305 (1879)

    Article  Google Scholar 

  4. E. Fischer, Ber. Dtsch. Chem. Ges. 26, 2400 (1893)

    Article  Google Scholar 

  5. W. Koenig, E. Knorr, Ber. Dtsch. Chem. Ges. 34, 957 (1901)

    Article  Google Scholar 

  6. H. Paulsen, Angew. Chem. Int. Ed. Engl. 21, 155 (1982)

    Article  Google Scholar 

  7. D.P. Galonic, D.Y. Gin, Nature 446, 1000 (2007)

    Article  CAS  Google Scholar 

  8. K. Larsen, K. Worm-Leonhard, P. Olsen, A. Hoel, K.J. Jensen, Org. Biomol. Chem. 3, 3966 (2005)

    Article  CAS  Google Scholar 

  9. M. Takatani, J. Nakano, M.A. Arai, A. Ishiwata, H. Ohta, Y. Ito, Tetrahedron Lett. 45, 3929 (2004)

    Article  CAS  Google Scholar 

  10. A.V. Demchenko, Lett. Org. Chem. 2, 580 (2005)

    Article  CAS  Google Scholar 

  11. K. Jansson, S. Ahlfors, T. Frejd, J. Kihlberg, G. Magnusson, J. Org. Chem. 53, 5629 (1988)

    Article  CAS  Google Scholar 

  12. H. Shimizu, J.M. Brown, S.W. Homans, R.A. Field, Tetrahedron 54, 9489 (1998)

    Article  CAS  Google Scholar 

  13. M.P. DeNinno, J.B. Etienne, K.C. Duplantie, Tetrahedron Lett. 36, 669 (1995)

    Article  CAS  Google Scholar 

  14. K. Jansson, G. Noori, G. Magnusson, J. Org. Chem. 55, 3181 (1990)

    Article  CAS  Google Scholar 

  15. V. Pozsgay, E.P. Dubois, L. Pannell, J. Org. Chem. 62, 2832 (1997)

    Article  CAS  Google Scholar 

  16. Y. Zhang, D. Dong, T. Zhou, Y. Zhang, Tetrahedron 66, 7373 (2010)

    Article  CAS  Google Scholar 

Download references

Acknowledgments

We thank Daowan Lai for his valuable advice. Financial support from the China Scholarship Council for a PhD fellowship to Huanhuan Qu is gratefully acknowledged.

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Authors and Affiliations

  1. Institut Parisien de Chimie Moléculaire (UMR CNRS 7201), Université Pierre et Marie Curie-Paris 6, C.181, 4 Place Jussieu, 75005, Paris, France

    Huanhuan Qu, Matthieu Sollogoub & Yongmin Zhang

  2. Glycochemistry & Glycobiology Lab, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zu Chong Zhi Road, Pudong, Shanghai, 201203, People’s Republic of China

    Huanhuan Qu

  3. Biomedicine Key Laboratory of Shaanxi Province, Northwest University, Xi’an, 710069, People’s Republic of China

    Huanhuan Qu & Wenji Sun

  4. Key Laboratory of Colloid and Interface Chemistry, Ministry of Education, School of Chemistry and Chemical Engineering, Shandong University, Jinan, 250100, People’s Republic of China

    Tao Sun

Authors
  1. Huanhuan Qu
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  2. Wenji Sun
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  3. Tao Sun
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  4. Matthieu Sollogoub
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  5. Yongmin Zhang
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Correspondence to Huanhuan Qu.

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Qu, H., Sun, W., Sun, T. et al. Synthesis and characterization of four novel 2-(trimethylsilyl)ethyl glycosides. Res Chem Intermed 41, 1107–1113 (2015). https://doi.org/10.1007/s11164-013-1257-2

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  • DOI: https://doi.org/10.1007/s11164-013-1257-2

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