Preparation of 2-O-arachidonoyl-1-O-stearoyl-sn-glycerol and other di-O-acyl glycerol derivatives

Tetrahedron Letters

Volumn 38, Issue 14, 1997, Pages 2539-2542

  Gaffney, Piers R J ^a   Reese, Colin B ^a  

^a KING'S COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

GLYCEROL DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030956223     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00395-X     Document Type: Article

References (19)

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3. Jung M.E., Shaw T.J. J. Am. Chem. Soc. 102:1980;6304-6311.
4. 5N).
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7. 13C NMR spectroscopic analysis of the resulting products suggested that both of them were obtained in a diastereoisomerically-pure state.
8. Brown, J.M.; Christodoulou, C.; Reese, C.B.; Sindona, G. J. Chem. Soc., Perkin Trans 1, 1984, 1785-1790.
9. 3 solution (6 : 94 v/v) had been allowed to stand at 22°C for 4 days.
10. 20 = - 7.1° (c 2.5, toluene).
11. Reese C.B., Serafinowska H.T., Zappia G. Tetrahedron Lett. 27:1986;2291-2294.
12. 3) of the latter derivative revealed a very strong signal at δ 68.58 and a very weak signal at δ 68.72. These signals were assigned to the C-2 resonances of the camphanyl derivatives of 2 and 3, respectively. Using the same analytical procedure, the enantiomeric excess of 2-O-arachidonoyl-3-O-stearoyl-sn-glycerol 3 was estimated to be ca. 90%. This preparation has not been optimized.
13. In order to minimize acyl migration, it is generally advisable to add a small quantity of acetic (or equivalent) acid to the eluting solvent in the chromatography of mono- and di-esters of glycerol.
14. Baldwin J.J., Raab M.W., Mensler K., Arison B.H., McClure D.E. J. Org. Chem. 43:1978;4876-4878.
15. 2SO] includes the following signals: 63.73, 65.52, 70.94.
16. Markiewicz W.T., Samek Z., Smrt J. Tetrahedron Lett. 21:1980;4523-4524.
17. 3] 62.81, 73.00, 76.06, 116.55, 123.25, 123.60, 126.85, 127.14, 127.77, 129.73, 130.44, 148.13, 151.15.
18. 3] includes the following signals: 61.11, 62.15, 71.95, 127.77, 127.94, 129.80, 130.02, 173.32, 173.62.
19. 3] 14.11, 22.61, 24.89, 25.65, 27.22, 29.12, 29.19, 29.38, 29.62, 31.55, 34.11, 65.05, 68.32, 127.92, 128.09, 130.03, 130.24, 173.97.