Facile synthesis and stabilization of 2-arachidonylglycerol via its 1,3- phenylboronate ester

Tetrahedron Letters

Volumn 41, Issue 19, 2000, Pages 3589-3592

  Seltzman, Herbert H ^a   Fleming, Denise N ^a   Hawkins, Gregory D ^a   Carroll, F Ivy ^a  

^a RTI INTERNATIONAL   (United States)

Author keywords

1,3 phenylboronate ester; 2 acylglycerols; Stability

Indexed keywords

2 ARACHIDONOYLGLYCEROL; 2 ARACHIDONOYLGLYCEROL 1,3 PHENYLBORONIC ACID ESTER; ACYLGLYCEROL; ESTER DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; ISOMERISM; MOLECULAR STABILITY; OXIDATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0034612166     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00469-X     Document Type: Article

References (13)

1. Mechoulam, R.; Ben-Shabat, S.; Hanus, L.; Ligumsky, M.; Kaminski, N. E.; Schatz, A. R.; Gopher, A.; Almog, S.; Martin, B. R.; Compton, D. R.; Pertwee, R. G.; Griffin, G.; Bayewitch, M.; Barg, J.; Vogel, Z. Biochem. Pharmacol. 1995, 50, 83-90.
2. Mechoulam, R.; Fride, E.; Di Marzo, V. Eur. J. Pharmaco. 1998, 359, 1-18.
3. Di Marzo, V.; Bisogno, T.; De Petrocellis, L.; Melck, D.; Martin, B. R. Cur. Med. Chem. 1999, 6, 721-744.
4. Martin, J. B. J. Am. Chem. Soc. 1953, 75, 5483-5486.
5. Martin, J. B. J. Am. Chem. Soc. 1953, 75, 5482-5483.
6. 2O, immediate).
7. +).
8. 3).
9. 3).
10. In chemical transformations, boronate esters have been used as protecting groups, which have generally been isolated by crystallization and distillation. The use of adsorption chromatography to separate boronate ester derivatives of compounds is less often seen. Chromatographically they have been used mostly for GC and for TLC where it is employed in the eluant to alter the mobility of various polyols. For a review of the applications of boronate esters, see: Ferrier, R. J. Adv. in Carbohy. Chem. Biochem. 1978, 35, 31-80.
11. 2O, 214 nm detection, 2 mL/min, Rt: 2-Ara-Gl 12.5 min, 1-Ara-Gl 13.9 min.
12. Merck LoBar C18 reversed phase size A column.
13. 3): 173.8, 130.5, 129.0, 128.8, 128.6, 128.3, 128.1, 127.8, 127.5, 75.1, 62.5, 33.7, 31.5, 29.3, 27.2, 26.5, 25.64, 25.62, 24.8, 22.6, 14.1.