152
J.A. Boomer, D.H. Thompson / Chemistry and Physics of Lipids 99 (1999) 145–153
4.9. O-(1,2-O-1Z%,9Z%-octadecadiene-sn-glycerol)-
N-(di-2-pthalamidyl ethyl amino)carbamate (9)
(dd, J1=10 hz, J2=6 hz, 1H), 4.29 (dd, J1=10
hz, J2=6 hz, 1H), 4.43 (m, 2H), 5.50 (m, 4H),
5.83 (d, J=6 hz, 1H), 5.92 (d, J=6 hz, 1H).
13C-NMR (C6D6): 14.4, 23.1, 24.5, 27.7, 29.7–
30.2, 32.3, 36.0, 40.9, 41.1, 50.1, 50.3, 64.4, 71.5,
79.1, 107.1, 107.6, 107.8, 130.1, 144.8, 145.4,
156.2. IR (neat): 723, 769, 1110, 1196, 1257, 1378,
1423, 1466, 1665, 1701, 2854, 2925, 3360, 3371.
1,2-O-(1Z%,9Z%-Octadecadienyl)-sn-glycerol (6,
308 mg, 0.523 mmol), 2,2%-dipyridyl carbonate
(274 mg, 1.26 mmol), and triethylamine (1.0 ml,
7.18 mmol) were stirred for 3 days in 10 ml
CH2Cl2. The reaction mixture was extracted with
25 ml NaHCO3 followed by 25 ml saturated
NaCl. The CH2Cl2 layer was dried over Na2SO4,
filtered, and evaporated. The resulting oil was
dissolved in CH2Cl2 (10 ml). 1,5-Dipthalamidyldi-
ethylenetriamine (315 mg, 0.868 mmol) was added
and the reaction stirred for 3 days. The solution
was evaporated and the crude mixture purified via
flash chromatography (3:2 hexane:ether), yielding
350 mg of a clear oil (69% yield). TLC (1:2
hexane: ether, UV, acidic molybdate): Rf=0.27.
1H-NMR (C6D6): 0.91 (t, J=7 hz, 6H), 1.2–1.55
(m, 40H), 2.08 (m, 8H), 2.28 (m, 4H), 3.39 (m,
4H), 3.58 (m, 4H), 3.68 (d, J=5 hz, 2H), 3.79 (p,
J=5 hz, 1H), 3.98 (d, J=5 hz, 2H), 4.45 (m,
2H), 5.50 (m, 4H), 6.02 (m, 2H), 6.89 (m, 4H),
7.47 (m, 4H). 13C-NMR (C6D6): 14.3, 23.1, 24.5,
27.7, 29.7–30.3, 32.3, 36.0, 45.5, 46.5, 64.5, 71.7,
78.9, 107.3, 107.8, 123.0, 130.1, 130.3, 132.4,
132.7, 133.4, 133.6, 144.9, 145.8, 155.9, 167.7,
168.0. IR (neat): 715, 873, 1111, 1200, 1450, 1467,
1700, 1717, 1774, 2923.
Acknowledgements
The authors wish to thank Drs Yuanjin Rui
and Sean Sullivan for their assistance with the
synthesis and Aniruddha Patwardhan for his in-
vigorating discussions. This work was kindly sup-
ported by NIH grant 1 R01GM55266-01A2.
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O-(1,2-O-1Z%,9Z%-octadecadiene-sn-glycerol)-N-
(di-2-pthalamidyl ethyl amino)carbamate (9, 306
mg, 0.313) was dissolved in 60 ml methanol and
hydrazine hydrate (100 ml, 2.1 mmol) added. The
reaction was stirred for 2 days. The solution was
evaporated, yielding an off white precipitate.
Chloroform (50 ml) was added and the precipitate
side product removed via filtration. The filtrate
was evaporated then dried in vacuo overnight
yielding 179 mg of a faint yellow oil (80% yield).
TLC (80:19.5:0.5 CHCl3:MeOH: NH4OH, molyb-
dic acid/heat, I2): Rf=0.85. 1H-NMR (C6D6):
0.91 (t, J=6 hz, 6H), 1.15–1.55 (m, 40 H), 2.08
(m, 8H), 2.28 (m, 4H), 2.58 (bs, 4H), 2.9–3.2 (m,
4H), 3.58 (m, 2H), 3.79 (p, J=5 hz, 1H), 4.19