1,2-DIPALMITOYL-SN-GLYCEROL synthesis

6synthesis methods

Product Name:1,2-DIPALMITOYL-SN-GLYCEROL
CAS Number:30334-71-5
Molecular formula:C35H68O5
Molecular Weight:568.91

30403-51-1 Synthesis

1,2-di-O-hexacecanoyl-3-O-benzyl-sn-glycerol

30403-51-1
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30334-71-5
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Yield:30334-71-5 99%

Reaction Conditions:

with hydrogen;palladium 10% on activated carbon in ethanol;dichloromethane at 20; for 4 h;

Steps:

1.1
The compound 8 (890 mg, 1.35 mmol) is dissolved in a CH₂Cl₂/EtOH mixture (1/1.5, 25 ml). A large excess of palladium-on-carbon (Pd/C 10%) is added and the reaction is stirred for 4 h at ambient temperature (approximately 20° C.) under atmospheric hydrogen pressure (balloon). The reaction mixture is heated to 40° C. for better dissolution of the expected product and then the catalyst is removed by filtration through a millipore membrane. The solid is rinsed three times with 20 ml of CH₂Cl₂/EtOH mixture (1/1) preheated to 40° C. The residual solvents are evaporated off under vacuum, so as to result in the expected compound 9 (757 mg, 99%) in the form of a white solid.C₂₅H₆₈O₅(M=568.93 g/mol).¹H NMR (250 MHz, CDCl₂) δ 0.88 (t, 6H, 2 CH₂, J=6.8 Hz), 1.26 (m, 48H, 24 CH₂), 1.62 (m, 4H, 2H3), 1.99 (t, 1H, OH, J=6.5 Hz), 2.32 (t, 2H, J=7.7 Hz), 2.35 (t, 2H, J=7.5 Hz), 3.73 (dd, 2H, 2H3a, J=5 and 6.2 Hz), 4.23 (dd, 1H, H1a_A, J_1aA-1aB=12 Hz, J_1A-2a=5.5 Hz), 4.35 (dd, 1H, H1a_B, J_1aB-2a=4.5 Hz), 5.08 (m, 1H, H2a).SI-MS: M calculated 568.51; found: 570.0 [M+H]⁺, 587.0 [M+NH₄]⁺, 592.0 [M+Na]⁺.