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

Method for synthesizing high-enantiomer-purity diprionidae pheromone and stereo isomer

A technology of stereoisomers and synthesis methods, which is applied in the field of synthesis of high-enantiomer pure pine sawfly sex pheromones and stereoisomers, can solve the problem of low activity and achieve high enantiomeric purity and good application foreground effect

Inactive Publication Date: 2011-08-31
XIAMEN UNIV
View PDF4 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] In addition, many other research groups have reported the synthesis of 3,7-dimethyl-2-pentadecanol and its carboxylate, but many are racemates, or other less active isomers

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
  • Method for synthesizing high-enantiomer-purity diprionidae pheromone and stereo isomer
  • Method for synthesizing high-enantiomer-purity diprionidae pheromone and stereo isomer
  • Method for synthesizing high-enantiomer-purity diprionidae pheromone and stereo isomer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Step 1 Synthesis of (3R)-Methanesulfonate Butyrate Ethyl 11

[0043] 300 mL of dichloromethane was added to a single-necked flask containing ethyl (3R)-hydroxybutyrate (20.29 g, 153.5 mmol). Under ice bath, pyridine (24.3mL, 184.2mmol) and methanesulfonyl chloride (13.74g, 176.5mmol) were added dropwise to the solution in the single-necked flask. After stirring for 15 min at the same temperature, the mixture was filtered with suction to remove pyridine hydrochloride. The filtrate was concentrated under reduced pressure and subjected to flash column chromatography (ethyl acetate: petroleum ether = 1:3) to obtain compound 11, 27.7 g of a colorless oil, with a yield of 86%.

[0044] Step 2 Synthesis of (3S)-hydroxybutyrate ethyl 8b

[0045] Calcium carbonate (4.3 g, 43.0 mmol) was added to water (108 mL) and stirred to form a suspension. Then the above solution was heated to 80° C., compound 11 (30.13 g, 143.3 mmol) was added dropwise at this temperature, and stirring was cont...

Embodiment 2

[0067] Step 1 (2R, 3R)-2-Methyl-3-hydroxybutyrate 9a

[0068] Under an ice bath, n-butyllithium (2.5M, 9.4 mL) was added dropwise to a solution of diisopropylamine (3.2 mL, 23.4 mmol) in tetrahydrofuran (6 mL). The mixture was cooled to -60°C, and a solution of 8a (1.40 g, 10.6 mmol) in tetrahydrofuran (2 mL) was added dropwise for 15 minutes. After 15 minutes, a mixed solution of methyl iodide (1.2 mL, 25.7 mmol) and hexamethylphosphoramide (1.5 mL) was added dropwise. After the mixture was stirred for 1 h, it was quenched with frozen saturated ammonium chloride (1.0 mL) and water (10 mL), and extracted with ethyl acetate (3×8 mL). The combined organic phase was washed sequentially with saturated brine (2 mL), dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure, and subjected to flash column chromatography (ethyl acetate: petroleum ether = 1:2) to obtain 1.13 g of a colorless oil Compound 9a, the yield was 72%.

[0069] Step 2 (2S, 3R)-2-methyl-3-...

Embodiment 3

[0088] Step 1 Synthesis of (3R)-Methanesulfonate Butyrate Ethyl 11

[0089] The synthesis method of (3R)-ethyl methanesulfonate butyrate 11 is the same as in Example 1.

[0090] Step 2 Synthesis of (3S)-hydroxybutyrate ethyl 8b

[0091] The synthesis method of (3S)-hydroxybutyrate ethyl 8b is the same as in Example 1.

[0092] Step 3 (2S, 3S)-2-methyl-3-hydroxybutyric acid ethyl ester 9b

[0093] The synthesis method of (2S, 3S)-2-methyl-3-hydroxybutyrate 9b is the same as in Example 1.

[0094] Step 4 (2R, 3S)-2-methyl-3-tetrahydropyranyl-1-butanol 10b

[0095] The synthesis method of (2R, 3S)-2-methyl-3-tetrahydropyranyl-1-butanol 10b is the same as in Example 1.

[0096] Step 5 (2R, 3S)-2-methyl-3-tetrahydropyranyl-1-p-toluenesulfonyloxybutane 6d

[0097] The synthesis method of (2R, 3S)-2-methyl-3-tetrahydropyranyl-1-p-toluenesulfonyloxybutane 6d is the same as in Example 1.

[0098] Step 6 (R)-1,3-Butanediol 12a

[0099] The synthesis method of (R)-1,3-butanediol 12a is the same as in Ex...

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 method for synthesizing a high-enantiomer-purity diprionidae pheromone and a stereo isomer, relates to a diprionidae pheromone and provides a novel method for synthesizing an optically-active high-enantiomer-purity diprionidae pheromone and a stereo isomer. The method comprises the following steps of: selectively synthesizing the high-enantiomer-purity diprionidae pheromone, a homologous compound thereof and the stereo isomer by taking malic acid or (3R)-hydroxy ethyl butyrate as a raw material; and synthesizing a series of important intermediate compounds, including(R)-1,3-butanediol 12a, (S)-1,3-butanediol 12b, (R)-3-methyl-1-bromotridecane 20a (S)-3-methyl-1-bromotridecane 20b as well as chiral 3,7-dimethyl-2-pentadecyl alcohol 21-28, chiral 3,7-dimethyl-2-tridecyl alcohol 29-36 and chiral 3,7-dimethyl-2-undecyl alcohol 37-44. The diprionidae pheromone is obtained by acylating chiral alcohol 21-44.

Description

Technical field [0001] The invention relates to the sex pheromone of the pine sawfly, in particular to a method for synthesizing the sex pheromone and stereoisomers of the high enantiomeric pure pine sawfly. Background technique [0002] The chemical connection between organisms is a universal law, and the chemical connection between insects is currently the most detailed research. Insects can not only attract the opposite sex, alert, mark paths and nests by releasing small amounts of chemical substances, and affect the development and behavior of other individuals of the same species, but also use chemical substances as weapons for offensive, defensive, and protection of the population. Insect pheromone (pheromone) is a micro-chemical substance secreted by an individual organism to the outside world and received by another body of the same species, which can cause specific behavior or development. Pheromone of insects can be divided into sex pheromone, aggregation pheromone, al...

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
IPC IPC(8): C07C69/06C07C69/14C07C67/08
Inventor 黄培强郑剑峰彭启龙张真蓝洪桥肖振华杨瑞峰庹世川胡孔珍项勇刚危祯
Owner XIAMEN UNIV
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