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Pristane synthesizing method

A synthetic method, pristane technology, applied in the field of biological reagents, to achieve the effect of low cost of raw materials, cheap raw materials, high cost of separation and purification

Active Publication Date: 2015-11-04
SHENZHEN DIECKMANN TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] The purpose of the present invention is to reduce costs, improve process safety, solve the purification problem caused by isomerization in the original synthesis method, and be suitable for the synthetic method of pristane

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] (1) Oxidation reaction, synthesis of phyton 2:

[0035] First, add 250g of isophytol 1, 2L of acetone, and 50ml of acetic acid into a 5L reaction flask in sequence. Slowly add 501g KMnO in batches 4 . With the prolongation of the reaction time, there will be exothermic phenomenon gradually. Cool with a little water circulation until the addition is complete, continue the reaction for 5h, then heat at 60°C and continue the reaction for 5h, after the reaction is complete, filter, extract with ethyl acetate, and dry over anhydrous sodium sulfate . 212g of phyton 2 was obtained, yield: 93%.

[0036] The NMR spectrum of Phytoketone 2 is:

[0037] 1 HNMR (500MHz, CDCl 3 ): 2.42-2.38 (2H, t, CH2), 2.13 (3H, s, CH3), 1.54-1.51 (3H, m, CH), 1.26-1.25 (2H, m, CH2), 1.15-1.07 (16H, m, CH2), 0.88-0.84 (12H, m, CH3).

[0038] (2) Methyl Grignard reaction, synthesis of compound 3:

[0039] Put 200g of phyton 2 into a 3L dry reaction flask, vacuumize, fill with N2, add 1.5L o...

Embodiment 2

[0051] (1) Oxidation reaction, synthesis of phyton 2:

[0052] First, add 300g of isophytol 1, 2.5L of acetone, and 100ml of acetic acid into a 5L reaction flask in sequence. Slowly add 454g H in batches 2 Cr 2 o 7 . As the reaction time prolongs, exothermic phenomenon gradually occurs, and the reaction is continued for 6 hours until the feeding is completed, and the reaction is continued for 8 hours. The rest is the same as in Example 1, and the yield is 93%.

[0053] (2) Methyl Grignard reaction, synthesis of compound 3:

[0054] Put 200g of phyton 2 into a 3L dry reaction bottle, vacuumize and fill with N 2 , add 1.5L of anhydrous tetrahydrofuran, cool to -10°C, slowly add 298ml of 3mol / L methyl Grignard reagent MeMgCl dropwise, after the dropwise addition, naturally warm up to room temperature, continue stirring for 1h, and the rest are the same as in Example 1 , yield: 93%, b.p.: 323°C.

[0055] (3), sulfonylation reaction, synthesis of compound 4:

[0056] Add 18...

Embodiment 3

[0062] (1) Oxidation reaction, synthesis of phyton 2:

[0063] First, add 200g of isophytol 1, 1.5L of acetone, and 40ml of acetic acid into a 5L reaction flask in sequence. Slowly add 426gNaIO 4 . With the prolongation of the reaction time, there is a gradual exothermic phenomenon, and the water is circulated and cooled slightly until the addition is completed, and the reaction is continued for 4 hours, and then heated to 80° C. to continue the reaction for 4 hours. The rest is the same as in Example 1, and the yield is 95%.

[0064] (2) Methyl Grignard reaction, synthesis of compound 3:

[0065] Put 180g of phyton 2 into a 3L dry reaction bottle, vacuumize and fill with N 2 , add 1.5L of anhydrous tetrahydrofuran, cool to -10°C, slowly add 298ml of 3mol / L methyl Grignard reagent MeMgI dropwise, after the dropwise addition, naturally warm up to room temperature, continue stirring for 3h, and the rest are the same as in Example 1 , yield: 96%, b.p.: 322°C.

[0066] (3), s...

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Abstract

The present invention discloses a novel method for chemically synthesizing pristane with isophytol as a starting material. Isophytol is used, and pristane is prepared through oxidation, a methyl Grignard reaction, sulfonylation, halogenation and reduction. The method in the present invention, as compared with the conventional synthesizing method, adopts cheap raw materials, avoids high pressure hydrogenation reactions, and solves the problems of methyl migration caused by a dehydration reaction or isomerization caused by cyclization in the conventional synthesizing method. The method of the present invention is suitable for industrial production of pristane.

Description

technical field [0001] The invention belongs to the field of biological reagents, and in particular relates to a synthesis method of pristane. Background technique [0002] Pristane is a saturated terpenoid compound extracted from basking shark, a colorless oily liquid. As an immunosuppressant, it stimulates the autoimmune system of mice by injecting them into mice, and obtains anti-tumor monoclonal antibodies in the ascites of mice. The titer of this antibody is often 100-1000 times higher than that of the cultured cell supernatant. At present, the anti-tumor monoclonal antibody induced by pristane is expected to be used in clinical anti-tumor application, and has a very strong application prospect. [0003] Since the basking shark was listed as the second-class protected animal by the Washington International Convention in 2002. In view of the scarcity of natural resources and the increasing market demand, there is an urgent need for a mature synthesis process to solve ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C9/22C07C1/26
Inventor 杨超文
Owner SHENZHEN DIECKMANN TECH CO LTD
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