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

详细信息    查看全文

• 作者：Huanhuan Qu (1) (2) (3)
  Wenji Sun (3)
  Tao Sun (4)
  Matthieu Sollogoub (1)
  Yongmin Zhang (1)
  
  1. Institut Parisien de Chimie Mol茅culaire (UMR CNRS 7201) ; Universit茅 Pierre et Marie Curie-Paris 6 ; C.181 ; 4 Place Jussieu ; 75005 ; Paris ; France
  2. Glycochemistry & Glycobiology Lab ; Shanghai Institute of Materia Medica ; Chinese Academy of Sciences ; 555 Zu Chong Zhi Road ; Pudong ; Shanghai ; 201203 ; People鈥檚 Republic of China
  3. Biomedicine Key Laboratory of Shaanxi Province ; Northwest University ; Xi鈥檃n ; 710069 ; People鈥檚 Republic of China
  4. Key Laboratory of Colloid and Interface Chemistry ; Ministry of Education ; School of Chemistry and Chemical Engineering ; Shandong University ; Jinan ; 250100 ; People鈥檚 Republic of China
  
• 关键词：Total synthesis ; Structure elucidation ; Glycosides ; NMR spectroscopy ; Oligosaccharides
• 刊名：Research on Chemical Intermediates
• 出版年：2015
• 出版时间：February 2015
• 年：2015
• 卷：41
• 期：2
• 页码：1107-1113
• 全文大小：204 KB
• 参考文献：1. H. Pellissier, Tetrahedron 61, 2947 (2005) ank" title="It opens in new window">CrossRef
  2. G. Wulff, G. R枚hle, Angew. Chem. Int. Ed. Engl. 13, 157 (1974) anie.197401571" target="_blank" title="It opens in new window">CrossRef
  3. A. Michael, Am. Chem. J. 1, 305 (1879) ank" title="It opens in new window">CrossRef
  4. E. Fischer, Ber. Dtsch. Chem. Ges. 26, 2400 (1893) ank" title="It opens in new window">CrossRef
  5. W. Koenig, E. Knorr, Ber. Dtsch. Chem. Ges. 34, 957 (1901) ank" title="It opens in new window">CrossRef
  6. H. Paulsen, Angew. Chem. Int. Ed. Engl. 21, 155 (1982) anie.198201553" target="_blank" title="It opens in new window">CrossRef
  7. D.P. Galonic, D.Y. Gin, Nature 446, 1000 (2007) ank" title="It opens in new window">CrossRef
  8. K. Larsen, K. Worm-Leonhard, P. Olsen, A. Hoel, K.J. Jensen, Org. Biomol. Chem. 3, 3966 (2005) ank" title="It opens in new window">CrossRef
  9. M. Takatani, J. Nakano, M.A. Arai, A. Ishiwata, H. Ohta, Y. Ito, Tetrahedron Lett. 45, 3929 (2004) ank" title="It opens in new window">CrossRef
  10. A.V. Demchenko, Lett. Org. Chem. 2, 580 (2005) ank" title="It opens in new window">CrossRef
  11. K. Jansson, S. Ahlfors, T. Frejd, J. Kihlberg, G. Magnusson, J. Org. Chem. 53, 5629 (1988) ank" title="It opens in new window">CrossRef
  12. H. Shimizu, J.M. Brown, S.W. Homans, R.A. Field, Tetrahedron 54, 9489 (1998) ank" title="It opens in new window">CrossRef
  13. M.P. DeNinno, J.B. Etienne, K.C. Duplantie, Tetrahedron Lett. 36, 669 (1995) ank" title="It opens in new window">CrossRef
  14. K. Jansson, G. Noori, G. Magnusson, J. Org. Chem. 55, 3181 (1990) ank" title="It opens in new window">CrossRef
  15. V. Pozsgay, E.P. Dubois, L. Pannell, J. Org. Chem. 62, 2832 (1997) ank" title="It opens in new window">CrossRef
  16. Y. Zhang, D. Dong, T. Zhou, Y. Zhang, Tetrahedron 66, 7373 (2010) ank" title="It opens in new window">CrossRef
  
• 刊物类别：Chemistry and Materials Science
• 刊物主题：Chemistry
  Catalysis
  Physical Chemistry
  Inorganic Chemistry
  
• 出版者：Springer Netherlands
• ISSN：1568-5675

文摘

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.