Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

A kind of synthetic method of pristane

A synthesis method and pristane technology are applied in the field of biological reagents to achieve the effects of cheap raw materials, complicated operation and simple process

Active Publication Date: 2016-08-24
SHENZHEN DIECKMANN TECH CO LTD
View PDF2 Cites 0 Cited by
  • 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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • A kind of synthetic method of pristane
  • A kind of synthetic method of pristane
  • A kind of synthetic method of pristane

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] (1) Oxidation reaction, synthesis of phyton 2:

[0036] First, add 300g of isophytol 1, 3L of acetone, and 60ml of acetic acid into a 5L reaction flask in sequence. Slowly add 632g KMnO in batches 4 . With the prolongation of the reaction time, there will be exothermic phenomenon gradually. Cool with water circulation slightly 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 completed, filter, extract with ethyl acetate, and dry over anhydrous sodium sulfate , to obtain 262g phyton 2, yield: 96%, b.p.: 184°C / 11mmHg.

[0037] The NMR spectrum of Phytoketone 2 is:

[0038] 1 HNMR (500MHz, CDCl3 ): 2.43-2.39 (2H, t, CH2), 2.13 (3H, s, CH3), 1.54-1.50 (3H, m, CH), 1.26-1.25 (2H, m, CH2), 1.15-1.06 (16H, m, CH2), 0.89-0.84 (12H, m, CH3).

[0039] (2) Epoxidation reaction, synthesis of compound 3:

[0040] Add 190g of epoxidation reagent dimethyl methylene sulfonium sulfonium into a ...

Embodiment 2

[0054] (1) Oxidation reaction, synthesis of phyton 2:

[0055] First, add 300g of isophytol 1, 3L of acetone, and 60ml of acetic acid into a 5L reaction flask in sequence. Slowly add 545g H in batches 2 Cr 2 o 7 . 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 6 hours, and then heated at 50°C to continue the reaction for 8 hours, and the rest is the same as in Example 1, the yield: 97%.

[0056] (2) Epoxidation reaction, synthesis of compound 3:

[0057] Add 200g of dimethyl methylene sulfonium sulfonium into a 3L three-necked flask, fill it with N 2 , add 220ml of anhydrous DMSO, stir to dissolve, add 200g of phyton 2 and 1.5L of anhydrous THF in turn, stir for 30min, cool in an ice-water bath, add 48g of NaOH in batches, the color of the reaction system changes: brown-green-yellow, the addition is complete , The ice b...

Embodiment 3

[0067] (1) Oxidation reaction, synthesis of phyton 2:

[0068] First, add 300g of isophytol 1, 3L of acetone, and 60ml of acetic acid into a 5L reaction flask in sequence. Slowly add 450g NaIO in batches 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 at 80° C. for 4 hours. The rest is the same as in Example 1, and the yield is 93%.

[0069] (2) Epoxidation reaction, synthesis of compound 3:

[0070] 180g dimethylsulfide ylide was added to a 3L three-neck flask, filled with N 2 , add 180ml of anhydrous DMSO, stir to dissolve, add 180g of phyton 2 and 1.5L of anhydrous THF in turn, stir for 30min, cool in an ice-water bath, add 32gNaH in batches, the color of the reaction system changes: brown-green-yellow, the addition is complete, The ice bath was removed, the temperature was slowly raised to ...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses a novel method for chemically synthesizing pristane on the basis of a starting material isophytol. By the method, pristane is obtained by oxidizing isophytol and performing epoxidation, lewis acid open-loop reaction, sulfonylation, halogenation and reduction. Compared with a conventional synthesis method, the method has the advantages that the raw material is low in cost, high-pressure hydrogenation reaction is avoided, the problem of methyl transfer or cyclization isomerization caused by dehydration reaction in the conventional synthesis method is solved, and the method is suitable for the 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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(China)
IPC IPC(8): C07C9/22C07C1/26
Inventor 杨超文
Owner SHENZHEN DIECKMANN TECH CO LTD
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com