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Migration of an acetyl group in glucosamine and glucose derivatives by the action of butyllithium. The synthesis of an N-acetylglucosamine 4-phosphate derivative

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Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

The migration of the acetyl group from C4 to C6 occurs in partially acetylated derivatives of D-glucose and D-glucosamine upon reaction with butyllithium.

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Literature cited

  1. D. R. Bundle, H. J. Jennings, and C. P. Kenny, Carbohydr. Res.,26, 268 (1973).

    PubMed  Google Scholar 

  2. I. B. Naumova, Usp. Biol. Khim.,6, 199 (1964).

    Google Scholar 

  3. E. T. Rietschel, H.-W. Wollenweber, R. Russa, et al., Rev. Infect. Dis.,6, 432 (1984).

    PubMed  Google Scholar 

  4. M. Inage, H. Chaki, S. Kusumoto, and T. Shiba, Chem. Lett., 1281 (1982).

  5. C. Diolez, M. Mondange, S. Sarfati, et al., J. Chem. Soc., Perkin Trans. 1, 275 (1984).

    Google Scholar 

  6. N. K. Kochetkov, A. F. Bochkov, B. A. Dmitriev, et al., Carbohydrate Chemistry [in Russian], Khimiya, Moscow (1967), p. 132.

    Google Scholar 

  7. R. Albert, K. Dax, A. E. Stuetz, and H. J. Weidmann, J. Carbohydr. Chem.,2, 279 (1983).

    Google Scholar 

  8. W. A. Bonner, J. Am. Chem. Soc.,80, 3697 (1958).

    Google Scholar 

  9. V. I. Gorbach, E. V. Ivanchina, V. V. Isakov, et al., Bioorg. Khim.,8, 1670 (1982).

    Google Scholar 

  10. E. A. Talley, Methods in Carbohydrate Chemistry [Russian translation], Mir, Moscow (1967), p. 177.

    Google Scholar 

  11. R. Kuhn, F. Zilliken, and A. Gauhe, Chem. Ber.,86, 466 (1953).

    Google Scholar 

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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 9, pp. 2106-2109, September, 1987.

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Gorbach, V.I., Krasikova, I.N., Luk'yanov, P.A. et al. Migration of an acetyl group in glucosamine and glucose derivatives by the action of butyllithium. The synthesis of an N-acetylglucosamine 4-phosphate derivative. Russ Chem Bull 36, 1957–1960 (1987). https://doi.org/10.1007/BF00958357

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  • DOI: https://doi.org/10.1007/BF00958357

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