NEW TYPE OF CATIONIC GLYCEROPHOSPHOLIPIDS
1529
4.40 br.s (2H, CH3OCH2). Found, %: C 46.71, H
8.28, P 9.50. C38H80N4O16P3. Calculated, %: C 46.69,
H 8.25, P 9.51.
(3H, CH2CHCH2OP), 4.24 br.s (2H, CH3OCH2),
5.07 d (6H, OCH2C6H5, JPH 8.72 Hz), 7.37 m (15H,
OCH2C6H5). Found, %: C 52.03, H 6.68, P 8.55.
C47H71ClNO19P3. Calculated, %: C 52.15, H 6.61,
P 8.58.
3
Tris[1-[1,2-O-isopropylideneglycero-3-(diethyl-
amino)phosphinothioyloxy]ethyl]amine chloro-
methoxymethylate (XXIV). Yield 0.85 g (83%), nD20
Tris[1-[1,2-O-isopropylideneglycero-3-[(benzyl-
oxy)(diethylamino)phosphinothioyloxy]ethyl]amine
chloromethoxymethylate (XXVIII). Yield 1.05 g
(89%), n2D0 1.5264, Rf 0.83 (B), 0.41 (D). 31P NMR
1.5004, Rf 0.71 (C), 0.06 (D). 31P NMR spectrum,
,
P
1
ppm: 76.95 br.s. H NMR spectrum, , ppm: 1.11 t
3
(18H, NCH2CH3, JHH 7.06 Hz), 1.36 s (9H), 1.45 s
3
[9H, C(CH3)2], 2.99 br.t (6H, NCH2CH2O, JHH
1
spectrum, P, ppm: 66.57 br.s. H NMR spectrum, ,
3
5.98 Hz), 3.22 m (12H, NCH2CH3, JPH 14.04 Hz),
ppm: 1.34 s (9H), 1.41 s [9H, C(CH3)2], 2.98 br.t (6H,
NCH2CH2O), 3.75 m (3H), 3.96 m (3H, CH2CH
CH2OP), 3.99 m (6H, NCH2CH2O), 4.02 m (6H,
CH2CHCH2OP), 4.06 s (3H, CH3OCH2), 4.14 br.s
(2H, CH3OCH2), 4.24 m (3H, CH2CHCH2OP), 5.11 d
3.80 m (3H), 3.86 m (3H, CH2CHCH2OP), 3.89 s (3H,
CH3OCH2), 4.03 m (6H, CH2CHCH2OP), 4.07 m (6H,
NCH2CH2O), 4.32 m (3H, CH2CHCH2OP). Found, %:
C 44.38, H 7.94, P 9.02. C38H80ClN4O13P3S3. Cal-
culated, %: C 44.50, H 7.86, P 9.06.
3
(6H, OCH2C6H5, JPH 8.68 Hz), 7.37 m (15H,
Bis[1-[1,2-O-isopropylideneglycero-3-[(benzyl-
oxy)(diethylamino)phosphinoyloxy]ethyl]methyl-
amine chloromethoxymethylate (XXV). Yield 0.7 g
(91%), n2D0 1.5122, Rf 0.59 (C), ).11 (G). 31P NMR
OCH2C6H5). Found, %: C 49.90, H 6.37, P 8.23.
C47H71ClNO16P3S3. Calculated, %: C 49.93, H 6.33,
P 8.22.
1
ACKNOWLEDGMENT
spectrum, P, ppm: 0.98 br.s. H NMR spectrum, ,
ppm: 1.34 s (6H), 1.41 s [6H, C(CH3)2], 2.73 br.s
(3H, NCH3), 3.23 br.t (4H, NCH2CH2O), 3.70 m (2H),
3.99 m (2H, CH2CHCH2OP), 4.02 m (4H, NCH2
CH2O), 4.07 m (4H, CH2CHCH2OP), 4.12 s (3H,
CH3OCH2), 4.24 m (2H, CH2CHCH2OP), 4.45 br.s
The work was financially supported by the Russian
Foundation for Basic Research (project no. 01-03-
32459).
REFERENCES
3
(2H, CH3OCH2), 5.13 d (4H, OCH2C6H5, JPH
1. Evstigneeva, R.P., Zvonkova, E.N., Serebrenniko-
va, G.A., and Shvets, V.I., Khimiya lipidov (Che-
mistry of Lipids), Moscow: Khimiya, 1983, p. 296.
2. Paltauf, F. and Hermetter, A., Prog. Lipid. Res., 1994,
vol. 93, no. 3, pp. 239 328.
9.83 Hz), 7.41 m (10H, OCH2C6H5). Found, %: C
51.64, H 6.90, P 8.00. C33H52ClNO13P2. Calculated,
%: C 51.60, H 6.82, P 8.06.
Bis[1-[1,2-O-isopropylideneglycero-3-[(benzyl-
oxy)(diethylamino)phosphinothioyloxy]ethyl]me-
thylamine chloromethoxymethylate (XXVI). Yield
0.72 g (90%), nD20 1.5358, Rf 0.88 (C), 0.20 (D). 31P
3. Nifant’ev, E.E. and Predvoditelev, D.A., Usp. Khim.,
1994, vol. 63, no. 1, pp. 73 92.
4. Predvoditelev, D.A. and Nifant’ev, E.E., Zh. Org.
Khim., 1995, vol. 31, no. 12, pp. 1761 1785.
5. Kabanov, A.V. and Kabanov, V.A., Vysokomolek.
Soedin., 1994, vol. 36, no. 2, pp. 198 211.
6. Drakopoulou, E., Tsivgoulis, G.M., Murhopadhyay, A.,
and Brisson, A., Tetrahedron Lett., 2000, vol. 41,
no. 1, pp. 4131 4134.
7. Kulakov, V.I. and Dergousov, A.A., Khim. Prirod.
Soedin., 1990, no. 3, pp. 326 330.
8. Miller, A.D., Angew. Chem. Int. Ed. Engl., 1998,
vol. 37, nos. 13 14, pp. 1768 1785.
9. Maslov, M.A., Sycheva, E.V., Morozova, N.G., and
Serebrennikova, G.A., Izv. Ross. Akad. Nauk, Ser.
Khim., 2000, no. 3, pp. 385 400.
10. Levashov, A.V. and Klyachko, N.L., Izv. Ross. Akad.
Nauk, Ser. Khim., 2001, no. 10, pp. 1638 1648.
11. Predvoditelev, D.A., Podzhunas, G.A., and Ni-
fant’ev, E.E., Zh. Obshch. Khim., 1971, vol. 41,
no. 10, pp. 2195 2199.
1
NMR spectrum, P, ppm: 69.55 br.s. H NMR spec-
trum, , ppm: 1.34 s (6H), 1.12 s [6H, C(CH3)2],
2.75 br.s (3H, NCH3), 3.33 br.t (4H, NCH2CH2O,
3JHH 6.05 Hz), 3.68 m (2H), 3.93 m (2H, CH2CH
CH2OP), 4.02 m (4H, NCH2CH2O), 4.03 s (3H,
CH3OCH2), 4.04 m (4H, CH2CHCH2OP), 4.26 m (2H,
CH2CHCH2OP), 4.47 br.s (2H, CH3OCH2), 5.15 d
3
(4H, OCH2C6H5, JPH 10.59 Hz), 7.37 m (1H,
OCH2C6H5). Found, %: C 49.48, H 6.60, P 7.80.
C33H52ClNO11P2S2. Calculated, %: C 49.53, H 6.55,
P 7.74.
Tris[1-[1,2-O-isopropylideneglycero-3-[(benzyl-
oxy)(diethylamino)phosphinoyloxy]ethyl]amine
chloromethoxymethylate (XXVII). Yield 0.99 g
(92%), n2D0 1.5058, Rf 0.30 (C), 0.05 (D). 31P NMR
1
spectrum, P, ppm: 0.9 br.s. H NMR spectrum, ,
ppm: 1.30 s (9H), 1.38 [9H, C(CH3)2], 3.00 br.t (6H,
NCH2CH2O, 3JHH 5.51 Hz), 3.70 m (3H), 3.94 m (3H,
CH2CHCH2OP), 3.98 m (6H, CH2CHCH2OP), 4.02 s
(3H, CH3OCH2), 4.19 m (6H, NCH2CH2O), 4.23 m
12. Nifant’ev, E.E., Predvoditelev, D.A., and Gra-
chev, M.K., Bioorg. Khim., 1977, vol. 3, no. 1,
pp. 68 75.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 73 No. 10 2003