Abstract
New acetal-like and phosphacyclic lipids were synthesized on the basis of 2-hydroxymethyl-2-propylpropane-1,3-diol. The initial triol was initially treated with higher aldehydes to obtain the corresponding acetals, which were phosphorylated with chlorobis(diethylamino)phosphine. Intermediate phosphorodiamidites were oxidized (without isolation) with phenyliodane oxide or subjected to sulfurization or selenization. Bicyclic phosphite derived from 2-hydroxymethyl-2-propylpropane-1,3-diol was acylated with hexadecanoyl chloride to give 2-chloro-4-propyl-1,3,2-dioxaphosphinan-4-ylmethyl hexadecanoate, and methanolysis of the latter, followed by sulfurization, afforded 2-methoxy-5-propyl-2-thioxo-1,3,2λ5-dioxaphosphinan-5-ylmethyl hexadecanoate as a new phosphacyclic lipid.
Similar content being viewed by others
References
Evstigneeva, R.P., Zvonkova, E.N., Serebrennikova, G.A., and Shvets, V.I., Khimiya lipidov (Chemistry of Lipids), Moscow: Khimiya, 1983.
Savin, G.A., Kamneva, E.A., and Nifant’ev, E.E., Russ. J. Org. Chem., 2003, vol. 39, p. 1048.
Savin, G.A. and Kamneva, E.A., Russ. J. Org. Chem., 2005, vol. 41, p. 962.
Noth, H. and Vetter, H.J., Chem. Ber., 1961, vol. 94, p. 1505.
Nifant’ev, E.E. and Vasyanina, L.K., Spektroskopiya YaMR 31 P (31P NMR Spectroscopy), Moscow: Mosk. Gos. Ped. Inst. imeni V.I. Lenina, 1986, p. 37.
Savin, G.A., Predvoditelev, D.A., and Nifant’ev, E.E., Bioorg. Khim., 1991, vol. 17, p. 280.
Nifant’ev, E.E., Predvoditelev, D.A., and Savin, G.A., Zh. Obshch. Khim., 1992, vol. 62, p. 2445.
Smirnova, L.I., Malenkovskaya, M.A., Predvoditelev, D.A., and Nifant’ev, E.E., Zh. Org. Khim., 1980, vol. 16, p. 1170.
Nifant’ev, E.E., Predvoditelev, D.A., and Savin, G.A., Bioorg. Khim., 1991, vol. 17, p. 126.
Nifantyev, E.E., Predvoditelev, D.A., Rasadkina, E.N., and Bekker, A.R., Phosphorus Sulfur, 1987, vol. 34, p. 109.
Savin, G.A. and Kutsemako, O.M., Bioorg. Khim., 2005, vol. 31, p. 414.
Nifant’ev, E.E., Predvoditelev, D.A., and Fursenko, I.V., Zh. Obshch. Khim., 1980, vol. 51, p. 2435.
Kabachnik, M.I. and Rossiiskaya, P.A., Izv. Akad. Nauk SSSR, Ser. Khim., 1945, p. 364.
Martynov, I.V., Fetisov, V.I., and Sokolov, V.B., Itogi Nauki Tekh., Ser. Org. Khim., 1989, vol. 11, p. 34.
Nifant’ev, E.E., Predvoditelev, D.A., and Savin, G.A., Dokl. Akad. Nauk SSSR, 1991, vol. 320, p. 905.
Dittmer, J.C. and Lester, R.L., J. Lipid Res., 1964, vol. 5, p. 126.
Potapov, A.M., Krasil’nikova, E.A., Razumov, A.I., and Baigil’dina, S.Yu., Zh. Obshch. Khim., 1970, vol. 40, p. 564.
Author information
Authors and Affiliations
Corresponding author
Additional information
Original Russian Text © G.A. Savin, 2007, published in Zhurnal Organicheskoi Khimii, 2007, Vol. 43, No. 11, pp. 1617–1620.
Rights and permissions
About this article
Cite this article
Savin, G.A. 2-hydroxymethyl-2-propylpropane-1,3-diol in the synthesis of acetal-like and phosphacyclic lipids. Russ J Org Chem 43, 1612–1616 (2007). https://doi.org/10.1134/S1070428007110048
Received:
Issue Date:
DOI: https://doi.org/10.1134/S1070428007110048