reduced pressure to afford the crude Mosher ester 49, which was
examined next by 1H and 13C NMR without further purification.
Yield calcd for C33H49F3O7 (614.73): 0.553 g (90%, colourless oil);
Rf (pentane–toluene–EtOAc = 40 : 50 : 10, v/v/v) = 0.45.
1-Oleoyl-2,3-diacetyl-sn-glycerol 50. Obtained from 1-oleoyl-
2-acetyl-3-trichloroacetyl-sn-glycerol (28; 0.544 g, 1.00 mmol) via
42 and acetyl chloride (0.142 mL; 2.00 mmol). Overall yield:
0.418 g (95%, colourless oil); [a]2D0 = −1.25 (c 9.33, CHCl3). All
other physicochemical and spectral characteristics were identical
to those of 35 and 36.
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1-Palmitoyl-2-acetyl-3-oleoyl-sn-glycerol
51. Synthesized
from 1-trichloroacetyl-2-acetyl-3-oleoyl-sn-glycerol (29; 0.544 g;
1.00 mmol) via 43 and palmitoyl chloride (0.606 mL; 2.00 mmol).
Overall yield: 0.598 g (94%, colourless oil); [a]2D0 = 0.00 (c 8.69,
CHCl3). All other physicochemical and spectral characteristics
were identical to those of 37.
1-Oleoyl-2-palmitoyl-3-acetyl-sn-glycerol 52. Acquired from
1-oleoyl-2-trichloroacetyl-3-acetyl-sn-glycerol (33; 0.544 g,
1.00 mmol) via 47 and palmitoyl chloride (0.606 mL; 2.00 mmol).
Yield: 0.580 g (91%, colourless oil); Rf (pentane–toluene–EtOAc =
40 : 50 : 10, v/v/v) = 0.55; [a]2D0 = −0.64 (c 8.15, CHCl3); found:
C, 73.50; H, 11.31%. C39H72O6 (636.98) requires C, 73.54; H,
11.39%.
1-Oleoyl-2,3-palmitoyl-sn-glycerol 53. Obtained from 1-oleoyl-
2-trichloroacetyl-3-palmitoyl-sn-glycerol (34; 0.740 g; 1.00 mmol)
via 48 and palmitoyl chloride (0.606 mL; 2.00 mmol). Yield:
0.758 g (91%); white solid, mp 34.0–35.0 ◦C; Rf (pentane–toluene–
EtOAc = 40 : 50 : 10, v/v/v) = 0.54; [a]2D0 = 0.00 (c 7.05, CHCl3);
lit.28 mp 29.8–34.5 ◦C; found: C, 76.40; H, 12.12%. C53H100O6
(833.36) requires C, 76.39; H, 12.09%.
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Acknowledgements
Financial support from the Swedish Natural Science Research
Council and the Swedish Foundation for Strategic Research is
gratefully acknowledged.
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