Preparation of 2-O-Arachidonoyl-1-O-stearoyl-sn-glycerol and Other Di-O-Acyl Glycerol Derivatives

Author:

Gaffney Piers R.J,Reese Colin B

Publisher

Elsevier BV

Subject

Organic Chemistry,Drug Discovery,Biochemistry

Reference19 articles.

1. The identification of a novel inositol lipid, phosphatidylinostiol trisphosphate (PIP3), in rat cerebrum using in vivo techniques

2. Monolayer Studies with Synthetic Saturated, Mono- and Polyunsaturated Mixed 1,2-Diglycerides, 1,2-Diacylphosphatidylethanolamines and Phosphatidylcholines at the Air-Water-Interface

3. Total synthesis of (R)-glycerol acetonide and the antiepileptic and hypotensive drug (-)-.gamma.-amino-.beta.-hydroxybutyric acid (GABOB): use of vitamin C as a chiral starting material

4. 1-O-Stearoyl-sn-glycerol 6 (Found: C, 69.70; H, 11.97. Calc. for C21H42O4 · 0.2 H2O: C, 69.65; H, 11.8%) has m.p. 67.5 – 68.5°C and [α]D20 = + 3.66° (c 4, C5H5N) [lit.5 [α]D25 = + 3.55° (c 5.24, C5H5N)]; δH [CDCl3] includes the following signals: 3.57 (1 H, dd, J 5.9 and 11.5), 3.69 (1 H, dd, J 3.7 and 11.5), 3.92 (1 H, m), 4.16 (2 H, m); δC[CDCl3] includes the following signals: 63.42, 65.18 and 70.33. The enantiomeric 3-O-stearoyl-sn-glycerol has m.p. 68.5 – 69.5°C and [α]D20 = − 3.41° (c 4, C5H5N).

5. A new, asymmetric synthesis of lipids and phospholipids

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