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Glycosylation with Glycosyl p-Bromophenyl Phthalates as New Efficient Glycosyl Donors

  • Kwon, Soon-Young (Center for Bioactive Molecular Hybrids and Department of Chemistry, Yonsei University) ;
  • Lee, Bo-Young (Center for Bioactive Molecular Hybrids and Department of Chemistry, Yonsei University) ;
  • Jeon, Heung-Bae (Center for Bioactive Molecular Hybrids and Department of Chemistry, Yonsei University) ;
  • Kim, Kwan-Soo (Center for Bioactive Molecular Hybrids and Department of Chemistry, Yonsei University)
  • Published : 2005.05.20

Abstract

References

  1. Varki, A. Glycobiology 1993, 3, 97 https://doi.org/10.1093/glycob/3.2.97
  2. Dwek, R. A. Chem. Rev. 1996, 96, 683 https://doi.org/10.1021/cr940283b
  3. Bertozzi, C. R.; Kiessling, L. L. Science 2001, 291, 2357 https://doi.org/10.1126/science.1059820
  4. Garegg, P. J. Adv. Carbohydr. Chem. Biochem. 1997, 52, 179 https://doi.org/10.1016/S0065-2318(08)60091-8
  5. Kahne, D.; Walker, S.; Cheng, Y.; Engen, D. V. J. Am. Chem. Soc. 1989, 111, 6881 https://doi.org/10.1021/ja00199a081
  6. Danishefsky, S. J.; Bilodeau, M. T. Angew. Chem., Int. Ed. 1996, 35, 1380 https://doi.org/10.1002/anie.199613801
  7. Schmidt, R. R.; Kinzy, W. Adv. Carbohydr. Chem. Biochem. 1994, 50, 21 https://doi.org/10.1016/S0065-2318(08)60150-X
  8. Fraser-Reid, B.; Madsen, R. In Preparative Carbohydrate Chemistry; Hanessian, S., Ed.; Marcel Dekker, Inc.: New York, 1997; p 339
  9. Shimizu, M.; Togo, H.; Yokoyama, M. Synthesis 1998, 799
  10. Plante, O. J.; Palmacci, E. R.; Andrade, R. B.; Seeberger, P. H. J. Am. Chem. Soc. 2001, 123, 9545 https://doi.org/10.1021/ja016227r
  11. Hinklin, R. J.; Kiessling, L. L. J. Am. Chem. Soc. 2001, 123, 3379 https://doi.org/10.1021/ja005735i
  12. Davis, B. J.; Ward, S. J.; Rendle, P. M. Chem. Commun. 2001, 189
  13. Petersen, L.; Jensen, K. J. J. Org. Chem. 2001, 66, 6268 https://doi.org/10.1021/jo0057654
  14. Nguyen, H. M.; Chen, Y.; Duron, S. G.; Gin, D. Y. J. Am. Chem. Soc. 2001, 123, 8766 https://doi.org/10.1021/ja015968p
  15. Hadd, M. J.; Gervay, J. Carbohydr. Res. 1999, 320, 61 https://doi.org/10.1016/S0008-6215(99)00146-9
  16. Crich, D.; Sun, S. J. Am. Chem. Soc. 1998, 120, 435 https://doi.org/10.1021/ja9734814
  17. Crich, D.; Smith, M. J. Am. Chem. Soc. 2001, 123, 9015 https://doi.org/10.1021/ja0111481
  18. Kim, K. S.; Lee, M. E.; Cho, J. W. Bull. Korean Chem. Soc. 2004, 25, 139 https://doi.org/10.1007/s11814-008-0025-2
  19. Kim, K. S.; Kim, J. H.; Lee, Y. J.; Lee, Y. J.; Park, J. J. Am. Chem. Soc. 2001, 123, 8477 https://doi.org/10.1021/ja015842s
  20. Kim, K. S.; Park, J.; Lee, Y. J.; Seo, Y. S. Angew. Chem., Int. Ed. 2003, 42, 459 https://doi.org/10.1002/anie.200390139
  21. Kwon, Y. T.; Lee, Y. J.; Lee, K.; Kim, K. S. Org. Lett. 2004, 6, 3901 https://doi.org/10.1021/ol048648u
  22. Kim, K. S.; Kang, S. S.; Seo, Y. S.; Kim, H. J.; Lee, Y. J.; Jeong, K.-S. Synlett. 2003, 1311
  23. Kim, K. S.; Lee, Y. J.; Kim, H. Y.; Kang, S. S.; Kwon, S. Y. Org. Biomol. Chem. 2004, 2, 2408 https://doi.org/10.1039/b405793g

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  2. Gold-catalysed glycosylation reaction using an easily accessible leaving group vol.13, pp.18, 2015, https://doi.org/10.1039/C5OB00248F