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A kind of synthetic method of marine natural product (r)-24-methyl-pentacos-2,4,16-triyne-1,6-diol and its enantiomer

A technology of natural products and synthetic methods, applied in chemical instruments and methods, preparation of organic compounds, production of bulk chemicals, etc., can solve problems such as destroying precious marine resources, and achieve the advantages of shortening reaction routes, simple steps and increasing yields. Effect

Active Publication Date: 2016-08-24
北京颖泰嘉和分析技术有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the active substances extracted from sponge organisms are generally at the ppm level, so in order to obtain a sufficient amount of active substances, it is necessary to fish a large amount of sponge substances from the ocean to extract (for example, only 1 ton of sponge can be extracted 300 mg of halichondrin B), which has anti-tumor effects, but the resources of the ocean are not unlimited, and disorderly collection will definitely destroy precious and limited marine resources

Method used

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  • A kind of synthetic method of marine natural product (r)-24-methyl-pentacos-2,4,16-triyne-1,6-diol and its enantiomer
  • A kind of synthetic method of marine natural product (r)-24-methyl-pentacos-2,4,16-triyne-1,6-diol and its enantiomer
  • A kind of synthetic method of marine natural product (r)-24-methyl-pentacos-2,4,16-triyne-1,6-diol and its enantiomer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Example 1 Preparation of dodec-2-en-1-ol

[0027] Under nitrogen protection, hexamethylphosphoric triamide (42 mL) and anhydrous tetrahydrofuran (150 mL) were added to a 500 mL Shrek bottle equipped with magnetic stirring. After stirring evenly, add propynyl alcohol (5.61g, 100mmol.), stir the mixture and then cool down to -78°C, then slowly add n-butyllithium (80mL of 2.5M solution in hexane), and heat up to - Stir at 30°C for 90 minutes. Subsequently, 1-bromononane (22.8 g, 110 mmol) was slowly added dropwise, and the reaction was continued to stir for 12 h, during which the temperature was allowed to rise to room temperature. After the reaction was complete, deionized water (30 mL) was added to quench the reaction. The aqueous phase was extracted with ethyl acetate (50 mL×3), the organic phases were combined, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain a crude product. Finally, it was purified by silica gel column chromat...

Embodiment 2

[0028] Example 2 Preparation of 2-(dodeca-11-ynyl-1-oxy)tetrahydro-2H-pyran

[0029] At zero degrees, in a 500mL three-necked flask equipped with mechanical stirring, add 1,3-propanediamine (125mL) and sodium hydrogen (10.0g, 250mmol, 60% in mineral oil), and after stirring for 30 minutes, the system rises The temperature was raised to 70°C, after stirring for 60 minutes. After the system temperature dropped to room temperature, dodec-2-en-1-ol (9.1 g, 50 mmol) was slowly added in portions. The reaction continued to stir at 55°C overnight. After the reaction was complete, deionized water (10 mL) was added to quench the reaction. The aqueous phase was back-extracted with ethyl acetate (50 mL x 3), the organic phases were combined, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain a crude product, which was directly carried out to the next reaction. In a 200m there-necked flask equipped with electromagnetic stirring, the crude product, dih...

Embodiment 3

[0030] Example 3 Preparation of 2-((19-methyleicos-11-yn-1-yl)oxy)tetrahydro-2H-pyran

[0031] Under nitrogen protection, hexamethylphosphoric triamide (3.5 mL) and anhydrous tetrahydrofuran (30 mL) were added to a 100 m Shrek flask equipped with magnetic stirring. After stirring evenly, add 2-(dodeca-11-ynyl-1-oxy)tetrahydro-2H-pyran (1.3g, 5mmol.), stir the mixture and cool down to -78°C, then slowly add normal Butyllithium (4.0 mL of 2.5M solution in hexane, 10 mmol) was added dropwise, and the temperature was raised to -30°C and stirred for 90 minutes. Then 1-iodo-7-methyloctane (1.9 g, 7.5 mmol) was slowly added dropwise, and the reaction was continued to be stirred for 12 h, during which the temperature was allowed to rise to room temperature. After the reaction was complete, deionized water (30 mL) was added to quench the reaction. The aqueous phase was extracted with ethyl acetate (50 mL×3), the organic phases were combined, dried over anhydrous sodium sulfate, and c...

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Abstract

The invention discloses a synthetic method for a marine natural product (R)-24-methyl-pentacosa-2,4,16-trialkynyl-1, 6-diol and enantiomer thereof, which belongs to the field of chemical synthesis. According to the invention, propargyl alcohol is used as a starting material, and a plurality of steps of reactions like coupling, transposition, oxidation, selective reduction, asymmetric alkynylation addition, esterification and hydrolysis are carried out to synthesize the marine natural product and enantiomer thereof; a key step is that trimethyl silicon-based acetylene and alkynal undergo asymmetric addition so as to produce a high-optical purity alkynol fragment in one step; and long-chain iodoalkane added in the process of synthesis is prepared through a series of simple reactions including bromination, oxidation, esterification, reduction and the like, so reaction route is greatly shortened. The synthesis of the natural product provided by the invention is reported for the first time; the synthetic method has the characteristics of simple steps, high total yield, good product stereoselectivity, etc.; and the optical purities of the products with two configurations are both greater than 99% ee.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and in particular relates to the synthesis of a marine natural product (R)-24-methyl-pentacar-2,4,16-triyne-1,6-diol and its enantiomers method. Background technique [0002] As we all know, sponge-like natural products have a wide range of physiological activities such as anti-tumor, bactericidal, and anti-inflammatory, and have attracted the attention of scientists. (Nat.Prod.Rep.2002,19,1-48.;Nat.Prod.Rep.2004,21,1-49 . ), especially in recent years, 8 marine drugs have been listed internationally, and dozens of drug candidates are in various phases of clinical research. These data show that the marine drug industry is about to usher in a new stage of development. However, the active substances extracted from sponge organisms are generally at the ppm level, so in order to obtain a sufficient amount of active substances, it is necessary to extract a large amount of sponge substances from the...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C33/04C07C29/34C07C17/20C07C19/07
CPCY02P20/55
Inventor 郑冰刘飞鹏钟江春边庆花李硕宁周云李敏言
Owner 北京颖泰嘉和分析技术有限公司
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