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New method of synthesizing N-alkoxycarbonylalkylphosphoramidites

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Conclusions

  1. 1.

    The reaction of dialkyl N-dialkylphosphoramidites with alkyl esters ofα-amino acids leads to their transamidation.

  2. 2.

    The transamidation products undergo an isomerization reaction with alkyl halides.

  3. 3.

    The transamidation products add sulfur to the trivalent phosphorus.

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Literature cited

  1. 1.

    R. Burgada, Ann. chimie,8, No. 5–6, 347 (1963).

  2. 2.

    N. P. Grechkin and L. N. Grishina, Izv. AN SSSR, Ser. khim.,1965, 1502.

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    O. Mitsunobu, T. Ohashi, M. Kikuchi, and T. Mukaiyama, J. Chem. Soc. Japan,39, 214 (1966).

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    K. A. Petrov, É. E. Nifant'ev, T. N. Lysenko, and E. P. Evdakov, Zh. obshch. khimii,31, 2377 (1961).

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    P. I. Alimov and O. N. Fedorova, Izv. AN SSSR, Ser. khim.,1965, 1987.

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    G. W. Anderson, J. Blodinger, R. W. Joung, and A. D. Welcher, J. Amer. Chem. Soc.,74, 5304 (1952).

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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 4, pp. 939–940, April, 1967.

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Grechkin, N.P., Nikonorova, L.K. New method of synthesizing N-alkoxycarbonylalkylphosphoramidites. Russ Chem Bull 16, 911–912 (1967). https://doi.org/10.1007/BF00915691

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Keywords

  • Sulfur
  • Ester
  • Phosphorus
  • Halide
  • Alkyl Halide