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Approaches to intramolecular sialylation. 2. Synthesis of per-O-acetylated thioglycosides of N-acetylneuraminic acid containing an unprotected carboxy group

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Abstract

Various approaches to the synthesis of per-O-acetylated thioglycosides of N-acetylneuraminic acid (Neu5Ac) containing an unprotected carboxy group starting from the corresponding methyl esters were comparatively studied. One-step demethylation of methyl thioglycoside (LiI, Py, reflux) proceeded inefficiently in contrast to the analogous smooth reaction of phenyl thioglycoside. An indirect route to derivatives with a free carboxy group involving saponification followed by acetylation of hydroxy groups proved to be more efficient for methyl α-thioglycoside of Neu5Ac.

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References

  1. L. O. Kononov, D. A. Volodin, and G. Magnusson, Izv. Akad. Nauk, Ser. Khim., 2003, 1357 [Russ. Chem. Bull., Int. Ed., 2003, 52, 1434].

    Google Scholar 

  2. Glycosciences. Status and Perspectives, Eds. H.-J. Gabius and S. Gabius, Chapman and Hall, Weinheim, 1997, 631 pp.

  3. K.-H. Jung, M. Müller, and R. R. Schmidt, Chem. Rev., 2000, 100, 4423 (and references cited therein).

    Google Scholar 

  4. A. Hasegawa, H. Ohki, T. Nagahama, and H. Ishida, Carbohydr. Res., 1991, 21, 277.

    Google Scholar 

  5. A. Marra and P. Sinaÿ, Carbohydr. Res., 1989, 187, 35.

    Google Scholar 

  6. G.-J. Boons and A. V. Demchenko, Chem. Rev., 2000, 100, 4539 (and references cited therein).

    Google Scholar 

  7. J. McMurry, Org. React., 1976, 24, 187.

    Google Scholar 

  8. S. Sato, K. Furuhata, and H. Ogura, Chem. Pharm. Bull., 1988, 36, 4678.

    Google Scholar 

  9. Y. E. Tsvetkov and R. R. Schmidt, Carbohydr. Lett., 1996, 1.

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    L. O. Kononov

  2. Higher Chemical College of the Russian Academy of Sciences, 9 Miusskaya pl., 125047, Moscow, Russian Federation

    A. M. Shpirt

  3. Institute of Physical and Chemical Research (RIKEN), Hirosawa 2-1, Wako-shi, Saitama, 351-01, Japan

    Y. Ito & T. Ogawa

Authors
  1. L. O. Kononov
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  2. A. M. Shpirt
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  3. Y. Ito
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  4. T. Ogawa
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Kononov, L.O., Shpirt, A.M., Ito, Y. et al. Approaches to intramolecular sialylation. 2. Synthesis of per-O-acetylated thioglycosides of N-acetylneuraminic acid containing an unprotected carboxy group. Russian Chemical Bulletin 52, 1442–1446 (2003). https://doi.org/10.1023/A:1024855917480

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  • DOI: https://doi.org/10.1023/A:1024855917480

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