Abstract
The reaction of 1,4:3,6-dianhydro-D-sorbitol 5-nitrate with POCl3 afforded mono-and bis(5-O-nitro-1,4:3,6-dianhydro-D-sorbit-2-yl) phosphorochloridates, whose hydrolysis resulted in phosphoric acid mono-and diesters. The subsequent treatment of these compounds with bases gave sodium and cyclohexylammonium salts. The reactions of phosphorochloridates with phenol, pentaerythritol dibromohydrin, and ethylenimine in the presence of organic bases afford mixed phosphates and phosphoramidates.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
M. D. Mashkovskii, Lekarstvennye sredstva [Drugs], Novaya Volna, Moscow, 2005, 1206 pp. (in Russian).
V. G. Granik and N. B. Grigor’ev, Vestn. RFFI, 2002, 30, No. 4, 49 [RFBR Information Bulletin, 2002, 30, No. 4 (Engl. Transl.)].
L. T. Eremenko, G. V. Oreshko, G. V. Lagodzinskaya, G. G. Aleksandrov, and I. L. Eremenko, Izv. Akad. Nauk, Ser. Khim., 2006, 380 [Russ. Chem. Bull., Int. Ed., 2006, 55, 393].
V. G. Granik and N. B. Grigor’ev, Izv. Akad. Nauk, Ser. Khim., 2002, 1268 [Russ. Chem. Bull., Int. Ed., 2002, 51, 1375].
E. Fischer, Ber., 1914, 47, 3193.
M. Gulland and G. I. Hobday, J. Chem. Soc., 1940, 746.
P. T. Gilham and H. G. Khorana, J. Am. Chem. Soc., 1958, 80, 6212.
H. A. C. Montgomery and J. H. Turnbull, J. Chem. Soc., 1958, 1963.
H. Hayashi, J. Ikeda, T. Kuroda, K. Kubo, T. Sano, and F. Suzuki, Chem. Pharm. Bull., 1993, 41, 1091.
E. E. Nifant’ev, Khimiya fosfororganicheskikh soedinenii [Chemistry of Organophosphorus Compounds], Izd-vo MGU, Moscow, 1971, 352 pp. (in Russian).
Phosphorus-31 NMR: Principles and Applications, Ed. D. G. Gorenshtein, Academic Press, New York, 1984, 604 pp.
K. Mislow and M. Raban in Topics in Stereochemistry, Eds N. L. Allinger and E. L. Eliel, Intersci. Publ.-Wiley and Sons, New York, 1967.
J. A. Kanters, A. Schouten, G. J. Sterk, and M. H. de Jomg, J. Mol. Struct., 1993, 298, 113.
A. J. Gordon and R. A. Ford, The Chemists Companion. A Handbook of Practical Data, Techniques and References, J. Wiley and Sons, New York-London, 1972.
G. M. Sheldrick, SHELXS97, Program for the Solution of Crystal Structures, University of Göttingen, Germany, 1997.
G. M. Sheldrick, SHELXL97, Program for the Refinement of Crystal Structures, University of Göttingen, Germany, 1997.
Author information
Authors and Affiliations
Corresponding author
Additional information
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 2026–2032, October, 2007.
Rights and permissions
About this article
Cite this article
Eremenko, L.T., Oreshko, G.V., Lagodzinskaya, G.V. et al. Mono-and bis(5-O-nitro-1,4:3,6-dianhydro-D-sorbit-2-yl) phosphates: synthesis and reactions with hydroxy-and amino-containing compounds. Russ Chem Bull 56, 2097–2104 (2007). https://doi.org/10.1007/s11172-007-0327-2
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/s11172-007-0327-2