1,2-DISTEAROYL-SN-GLYCEROL synthesis

Yield:1429-59-0 354 mg

Reaction Conditions:

with palladium 10% on activated carbon;hydrogen in hexane at 20; under 3750.38 Torr; for 2 h;

Steps:

2,3-Dihexadecanoyl-sn-glycerol (R)-15

General procedure: To a solution of 1-O-benzyl-sn-glycerol (S)-10 (300mg, 1.65mmol) and hexanoic acid (928mg, 3.62mmol) in dried dichloromethane (4.0ml) were added DMAP (95mg, 0.78mmol) and EDAC (695mg, 3.63mmol). The resulting solution was stirred magnetically at rt until TLC monitoring (80:20:1 pet. ether/ether/acetic acid) indicated complete reaction. The reaction was stopped by passing the reaction mixture through a short column packed with silica gel using petroleum ether as an eluent. The solvent was removed in vacuo and the resulting residue without further purification was dissolved in n-hexane (50ml) and transferred to a hydrogenation flask followed by the addition of Pd/C catalyst (25mg). The reaction was performed at rt in a PARR reactor under hydrogen pressure (5bar). When the reaction was complete (2h), the catalyst was separated off by filtration with the aid of Celite and the solvent was removed in vacuo on a rotary evaporator. Recrystallization from n-hexane or petroleum ether afforded the product ( R)-15 as white crystals (695mg, 1.22mmol) in 74% overall yield.

References:

Kristinsson, Bjoern;Linderborg, Kaisa M.;Kallio, Heikki;Haraldsson, Gudmundur G. [Tetrahedron Asymmetry,2014,vol. 25,# 2,p. 125 - 132]