Preparation method of (R)-1,2-distearoyl phosphatidylcholine

A technology of stearoyl phosphatidyl choline and distearoyl, which is applied in the field of preparation of (R)-1,2-distearoyl phosphatidyl choline, which can solve the problem of unsuitability for industrial production and cumbersome reaction steps, etc. problems, to achieve the effects of industrial application, simplification of reaction steps, and mild reaction conditions

Active Publication Date: 2013-11-27
吉民
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method uses glycerol as a raw material, and it is necessary to protect and deprotect the dihydroxyl and monohydroxyl groups of the glycerol skeleton, and the reaction steps are cumbersome.
Not suitable for industrial production
And, this method makes the distearoylphosphatidylcholine of racemization, the preparation method of the single optical isomer of distearoylphosphatidylcholine has not yet been reported in the literature

Method used

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  • Preparation method of (R)-1,2-distearoyl phosphatidylcholine
  • Preparation method of (R)-1,2-distearoyl phosphatidylcholine
  • Preparation method of (R)-1,2-distearoyl phosphatidylcholine

Examples

Experimental program
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Embodiment 1

[0037] Embodiment 1, the preparation of (S)-1,2-diol-3-iodopropane

[0038] Add 0.08 g (0.1 mmol) of hydroquinidine 1,4-(2,3-naphthyridine) diether (DHQD) into a round bottom reaction flask 2 PHAL, 0.018g (0.05mmol) K 2 OSo 2 (OH) 4 , 9.8 g (30 mmol) K 3 Fe(CN) 6 , 4.2 g (30 mmol) K 2 CO 3 , 2.5 g (30 mmol) NaHCO 3 , 0.95g (10mmol) and 100mL of an aqueous solution of tert-butanol (tert-butanol: water = 1:1), stirred well at 0°C, then added 1.7g (10mmol) of 3-iodopropene to react for 6 hours, and added 10g Na 2 S 2 o 4And continue stirring for 30 minutes to stop the reaction. The aqueous layer was separated and extracted with ethyl acetate, and the combined organic layers were washed with 1N KOH, dilute hydrochloric acid and saturated brine, respectively. Dried over anhydrous magnesium sulfate and concentrated to obtain a crude product. Recrystallized from a mixed solvent of petroleum ether and methanol to obtain 1.58 g of (S)-1,2-diol-3-iodopropane with a yield of 7...

Embodiment 2

[0039] Embodiment 2, the preparation of (R)-1,2-distearoyl-3-iodopropane

[0040] Stearic anhydride (0.8g, 1.5mmol), (S)-1,2-diol-3-iodopropane (0.2g, 1mmol) was added to 50mL of dichloromethane, stirred and refluxed at 40°C under nitrogen protection for 3 Hours, stop heating, after cooling to room temperature, pour 50mL of anhydrous diethyl ether. The organic layer was washed with 10 mL of 5% aqueous sodium bicarbonate solution and 10 mL of saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain a crude product that was recrystallized with ethanol to obtain 0.61 g of (S)-1,2-diol-3 - iodopropane, yield 83%.

Embodiment 3

[0041] Example 3, Preparation of (R)-1,2-distearoyl-3-(3,4-dimethoxybenzyloxy)phosphate propane

[0042] (R)-1,2-Distearoyl-3-iodopropane (0.6g, 0.8mmol) and 3,4-dimethoxybenzyl silver phosphate (1.3g, 2.5mmol) were added under dark conditions into 50 mL of toluene, reflux for 6 h to stop the reaction, cool to room temperature, filter, wash with dichloromethane, combine the organic layers and concentrate under reduced pressure, and recrystallize the obtained crude product with ethanol to obtain 0.52 g of a white solid, with a yield of 65%.

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Abstract

The invention discloses a preparation method of (R)-1,2-distearoyl phosphatidylcholine. The preparation method of (R)-1,2-distearoyl phosphatidylcholine comprises the following steps of: with 3-halogenated propylene as a raw material, carrying out an oxidation reaction under the catalytic action of a chiral catalyst, carrying out an addition reaction on the obtained (S)-1,2-diol-3-halogenated propane and stearic anhydride or stearic acid halide to obtain (R)-1,2-distearoyl-3-halogenated propane; then carrying out a reflux reaction on the (R)-1,2-distearoyl-3-halogenated propane and 3,4-dimethoxy benzyl silver phosphate to obtain (R)-1,2-distearoyl-3-(3,4-dimethoxy benzyl) phosphate propane; carrying out reaction on the (R)-1,2-distearoyl-3-(3,4-dimethoxy benzyl) phosphate propane and a phase transfer catalyst to remove phosphorus protecting group, so as to obtain (R)-1,2-glycerol distearate-glycerol-3- phosphatidic acid; finally carrying out the addition reaction on the (R)-1,2-glycerol distearate-glycerol-3-phosphatidic acid and choline tosilate in anhydrous pyridine under the catalytic action of trichloroacetonitrile to obtain (R)-1,2-distearoyl phosphatidylcholine. The preparation method of (R)-1,2-distearoyl phosphatidylcholine is simple in steps, mild in reaction and applicable to industrial production.

Description

technical field [0001] The invention belongs to the field of medicine and chemical industry, and specifically relates to a preparation method of (R)-1,2-distearoylphosphatidylcholine. Background technique [0002] Phospholipids are an important part of biological membranes. The polar end containing phosphate is hydrophilic, and the non-polar ends of the two longer hydrocarbon chains are lipophilic. This unique physical and chemical property enables it to spontaneously dissolve in water. A closed bilayer is formed in the medium, which becomes a biomembrane skeleton and can be used as a liposome material in the pharmaceutical industry. However, as liposome materials, natural phospholipids have disadvantages such as short lifespan, easy oxidation, and poor stability, which limit their application. [0003] Distearoylphosphatidylcholine (1,2-Distearoyl-sn-glycero-3-phosphocholine, DSPC) is an important synthetic phospholipid, which is mainly used in the preparation of liposomes...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/10
CPCY02P20/55
Inventor 吉民蔡进顾宁李锐
Owner 吉民
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