1,2-dipalmitoyl-SN-glycerol-3-phosphoethanolamine and preparation method thereof

A technology of phosphoethanolamine and dipalmitin, which is applied in the field of compound preparation, can solve problems such as difficult removal, large polar impurities, and poor purity of the final product, and achieve less by-products, high selectivity, and high overall yield Effect

Inactive Publication Date: 2019-10-15
安徽昊帆生物有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0009] However, the above method generates more large polar impurities

Method used

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  • 1,2-dipalmitoyl-SN-glycerol-3-phosphoethanolamine and preparation method thereof
  • 1,2-dipalmitoyl-SN-glycerol-3-phosphoethanolamine and preparation method thereof
  • 1,2-dipalmitoyl-SN-glycerol-3-phosphoethanolamine and preparation method thereof

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Experimental program
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preparation example Construction

[0031] Such as figure 1 As shown, the preparation method of 1,2-dipalmitoyl-SN-glycerol-3-phosphoethanolamine according to the embodiment of the present invention includes the following steps:

[0032] Step S1, the dipalmitic acid glyceride under the action of tetrahydrofuran (THF) and alkali, and POCl 3 A nucleophilic substitution reaction occurs. After the reaction is completed, the reaction product is purified to obtain Intermediate 1, which is (R)-3-((dichlorophosphoryl)oxy)propane-1,2-di Palmitate.

[0033] Wherein, the base may be triethylamine (TEA), diisopropylethylamine (DIEA), pyridine, or a mixture thereof.

[0034] For example, as shown in the following formula (III), dipalmitic acid glyceride under the action of tetrahydrofuran and triethylamine, and POCl 3 A nucleophilic substitution reaction takes place to obtain intermediate 1 (ie (R)-3-((dichlorophosphoryl)oxy)propane-1,2-dipalmitate)

[0035]

[0036] Preferably, the dipalmitic acid glyceride: alkali: POCl 3 The mol...

example 1

[0055] In a 50ml round bottom flask, dissolve 3g dipalmitate in 10mL tetrahydrofuran, add 0.8g TEA; add 1.21g POCl 3 Dissolve in 20mL tetrahydrofuran, drip into the reaction system under ice water bath, keep the ice water bath for reaction. TLC monitors that the reaction is complete, the insoluble solid is removed by suction filtration, the mother liquor is evaporated to dryness under reduced pressure, 20 mL of acetonitrile is added to make a slurry, and 3 g of white solid is obtained by suction filtration, with a yield of 83%.

[0056] The reaction product was subjected to nuclear magnetic resonance experiments to confirm the structure of the product. The data are as follows:

[0057] 1 H NMR(500MHz, CDCl 3 )δ5.22--5.38(m,1H), 4.41-4.58(m,1H), 4.35-4.38(m,1H), 4.08-4.29(m,2H), 2.30-2.44(m,4H), 1.62- 1.67 (m, 4H), 1.14-1.45 (m, 48H), 0.90 (t, J = 6.9 Hz, 6H). The test result is consistent with the literature value.

example 2

[0059] In a 50ml round bottom flask, dissolve 3g dipalmitate glyceride in 10mL tetrahydrofuran, add 1g DIEA; add 1.21g POCl 3 Dissolve in 20mL tetrahydrofuran, drip into the reaction system under ice water bath, keep the ice water bath for reaction. TLC monitors the completion of the reaction, removes the insoluble solids by suction filtration, evaporates the mother liquor to dryness under reduced pressure, adds 20 mL of acetonitrile to make a slurry, and obtains 2.2 g of white solids by suction filtration. The yield is 61%.

[0060] The reaction product was subjected to nuclear magnetic resonance experiments to confirm the structure of the product. The data are as follows:

[0061] 1 H NMR(500MHz, CDCl 3 )δ5.22--5.38(m,1H), 4.41-4.58(m,1H), 4.35-4.38(m,1H), 4.08-4.29(m,2H), 2.30-2.44(m,4H), 1.62- 1.67 (m, 4H), 1.14-1.45 (m, 48H), 0.90 (t, J = 6.9 Hz, 6H). The test result is consistent with the literature value.

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Abstract

The invention provides 1,2-dipalmitoyl-SN-glycerol-3-phosphoethanolamine and a preparation method thereof. The preparation method comprises the following steps: S1, performing a nucleophilic substitution reaction on glyceryldipalmitate and POCl3 under the action of tetrahydrofuran and alkali, and purifying a reaction product after completion of the reaction to obtain an intermediate 1, wherein theintermediate 1 is (R)-3-((dichlorophosphoryl)oxy)propane-1,2-dipalmitic acid; S2, performing a nucleophilic substitution reaction on the intermediate 1 and N-Fmoc-ethanolamine under the action of tetrahydrofuran and alkali, and purifying a reaction product after completion of the reaction to obtain an intermediate 2, wherein the intermediate 2 is (R)-3-(((2-( fluorenylmethoxy carbonylamino)ethoxy)(hydroxy)phosphoryl)oxy)propane-1,2-dipalmitate; and S3, performing a nucleophilic substitution reaction on the intermediate 2 under the action of a solvent and alkali to obtain the 1,2-dipalmitoyl-SN-glycerol-3-phosphoethanolamine. According to the preparation method provided by the embodiment of the invention, a final product is relatively high in purity, and byproducts are few.

Description

Technical field [0001] The invention relates to the technical field of compound preparation, in particular to 1,2-dipalmitoyl-SN-glycerol-3-phosphoethanolamine (abbreviated as DPPE) and a preparation method thereof. Background technique [0002] Phospholipids are the general term for a class of phosphorus-containing lipid compounds. They are the main components of cell membranes and have important physiological functions. Studies in molecular biology and pharmacology have found that phospholipids are involved in many important life activities in organisms, such as cell signal transduction, nerve cell information transmission, lipoprotein metabolism and so on. After years of development, phospholipids have been widely used in the fields of food, cosmetics, health care products and pharmaceutical preparations, especially liposome technology. [0003] Among phospholipids, phosphatidylcholine has the most content, followed by phosphatidylethanolamine. Phosphatidylethanolamine has goo...

Claims

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Application Information

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IPC IPC(8): C07F9/14C07F9/09
CPCC07F9/091C07F9/14
Inventor 陆雪根李宏林江龙
Owner 安徽昊帆生物有限公司
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