Synthesis of 1-O-stearoyl-2-O-arachidonoyl-sn-glycer-3-yl-D-myo-inositol 3,4,5-trisphosphate and its stereoisomers

Bioorganic and Medicinal Chemistry Letters

Volumn 7, Issue 24, 1997, Pages 3171-3176

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

^a King's CollegeLondon ^*  (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

2 O ARACHIDONYL 1 O STEAROYLGLYCER 3 YL INOSITOL 3,4,5 TRISPHOSPHATE; INOSITOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOISOMERISM;

EID: 0031458504     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(97)10166-4     Document Type: Article

References (38)

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23. 2O is added, the signals at δ 2.53 and 2.77 (assigned to the resonances of the hydroxy protons) disappear, and the signals at δ 3.16 and 3.43 (assigned to the resonances of H-l and H-3) collapse to double-doublets (J 2.6 and 8.6, and 2.1 and 8.9, respectively). It is clear from the COSY spectrum of compound 11 that H-l and H-3 are both adjacent to H-2.
24. 13C NMR spectroscopic data that 13 and 14 are diastereoisomers and not regioisomers. Thus only two [indicated by (*)] of the above seven methine carbon resonance signals in 13 and 14 differ by more than 0.1 ppm. The position of the menthoxyacetyl group in 13 (i.e. whether it is on O-3 or O-l) is not firmly established but the l - hydroxy function of 11 is believed to be more hindered than its 3-hydroxy function.
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34. 3] -3.68, -3.37, -2.01, -1.81, -1.78, -1.75, -1.72, -1.68.
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36. 4 : 1125.5.
37. 2O (1 : 1 v/v)] 1.60, 2.51, 3.05, 3.33.
38. 2O (1 : 1 v/v)] 1.62, 2.50, 3.00, 3.34.