| Use | 1, 2-octadecyl-SN-glycerol is an organic intermediate, which can be prepared from (R)-( )-3-benzyloxy-1, 2-propanediol and octanoyl chloride were used as raw materials, acylated first, and benzyloxycarbonyl was fused to be removed to obtain 1, 2-octadecyl-SN-glycerol. 1, 2-octadecyl-SN-glycerol can be used to prepare the folate targeting molecule polyethylene glycol (2000Da) to 1, 2-octadecyl-SN-glycerol lipid material. |
| preparation | within ten minutes, to (R)-(+)-3-benzyloxy-1, to a solution of 2-propanediol (4.0g,21.95mmol) in anhydrous pyridine (40ml) was added dropwise octanoyl chloride (8.93g,54.87mmol) followed by DMAP(267 mg, 2.19 mmol). The reaction mixture was stirred at 55°C for 48 h, diluted with EtOAc(300ml), washed with water (100ml), 1N HCl(2x 100ml) and brine (100ml), dried (Na2SO4). And concentrated. The residue was purified on a SiO2 column (3%EtOAc/hexanes) to give 7.3g(75%) of product as a colorless slurry. Yield 7.3g(75%). A solution of the above oil (6.8g,15.66mmol) in EtOH:EtOAc:AcOH(9:1:0.1)(30ml), hydrogenation was carried out at 40psi in 10% Pd/C(900mg,10%) for 3 hours. The catalyst was filtered off on a bed of Celite and concentrated to give 1,2-octadecyl-SN-glycerol in yield (5.0,93%). |
