(R)-4-isopropyl-3-((R)-2-methyl-5-hexenoyl) oxazolidine-2-ketone and application thereof in synthesis of sex pheromone component of western inchworm cedar

Abstract

The invention discloses (R)-4-isopropyl-3-((R)-2-methyl-5-hexenoyl) oxazolidine-2-ketone and application of the (R)-4-isopropyl-3-((R)-2-methyl-5-hexenoyl) oxazolidine-2-ketone to synthesis of sex pheromone components of western inchworm cedar, and relates to the technical field of biological pesticides. According to the application, (R)-4-isopropyl-3-((R)-2-methyl-5-hexenoyl) oxazolidine-2-ketone is utilized to synthesize (5R, 11S)-5, 11-dimethyl heptadecane, the total yield can reach 18%, and the optical purity of (5R, 11S)-5, 11-dimethyl heptadecane is greater than 99%; the (S)-7-methylheptadecane is synthesized by using the (R)-4-isopropyl-3-((R)-2-methyl-5-hexenoyl) oxazolidine-2-ketone, the total yield can reach 30%, and the optical purity of the (5R, 11S)-5, 11-dimethylheptadecane is greater than 99%.

Description

Technical Field

[0001] The invention belongs to the technical field of biological pesticides, and specifically relates to (R)-4-isopropyl-3-((R)-2-methyl-5-hexenoyl)oxazolidin-2-one and application thereof in synthesizing sex pheromone components of western hemlock looper. Background Art 4-isopropyl-3-(2-methyl-5-hexenoyl)oxazolidin-2-one is a chiral building block commonly used in the fields of medicine, pesticides and material synthesis. In 2014, Brimble and his team published a paper entitled "Wadsworth, AD; Furkert, DP; Brimble, MA The Journal of Organic Chemistry 2014, 79, 11179-11193." The synthesis of (S)-4-isopropyl-3-((S)-2-methyl-5-hexenoyl)oxazolidin-2-one and (R)-4-isopropyl-3-((S)-2-methyl-5-hexenoyl)oxazolidin-2-one by the reaction of (S)-4-isopropyl-3-methacryloyloxazolidin-2-one with tributyl allylstannane catalyzed by titanium tetrachloride Lewis acid. However, there is no prior art that discloses the synthesis of (R)-4-isopropyl-3-((S)-2-methyl-5-hexenoyl)oxazolidin-2-one. The present invention discloses a compound of (R)-4-isopropyl-3-((R)-2-methyl-5-hexenoyl)oxazolidin-2-one. For this purpose, the present invention specifically develops a (R)-4-isopropyl-3-((R)-2-methyl-5-hexenoyl)oxazolidin-2-one, and prepares (5R,11S)-5,11-dimethylheptadecane (i.e., western hemlock looper sex pheromone component 1) and (S)-7-methylheptadecane (i.e., western hemlock looper sex pheromone component 2) based on (R)-4-isopropyl-3-((R)-2-methyl-5-hexenoyl)oxazolidin-2-one. Summary of the invention

[0003] In order to make up for the deficiencies of the prior art, the present invention provides a (R)-4-isopropyl-3-((R)-2-methyl-5-hexenoyl)oxazolidin-2-one and its application in synthesizing the sex pheromone component of western hemlock looper.

[0004] The technical solution of the present invention is: A (R)-4-isopropyl-3-((R)-2-methyl-5-hexenoyl)oxazolidin-2-one, wherein the structural formula of the (R)-4-isopropyl-3-((R)-2-methyl-5-hexenoyl)oxazolidin-2-one is as shown in Formula 7:

[0005] A method for synthesizing (R)-4-isopropyl-3-((R)-2-methyl-5-hexenoyl)oxazolidin-2-one, wherein the (R)-4-isopropyl-3-((R)-2-methyl-5-hexenoyl)oxazolidin-2-one is the above-mentioned (R)-4-isopropyl-3-((R)-2-methyl-5-hexenoyl)oxazolidin-2-one, and the method for synthesizing (R)-4-isopropyl-3-((R)-2-methyl-5-hexenoyl)oxazolidin-2-one comprises the following steps: S1, using 5-hexenoic acid as a starting material, reacting with (R)-4-isopropyloxazolidin-2-one to synthesize (R)-3-(5-hexenoyl)-4-isopropyloxazolidin-2-one; S2. Synthesize (R)-4-isopropyl-3-((R)-2-methyl-5-hexenoyl)oxazolidin-2-one by chiral-induced asymmetric methylation reaction.

[0006] Preferably, step S1 includes the following specific steps: S1-1, under argon protection and at 0-5°C, slowly add oxalyl chloride and dimethylformamide to a dichloromethane solution containing 5-hexenoic acid; then heat to room temperature, stir and react for 2-4 hours, and concentrate under reduced pressure to remove the solvent to obtain a slightly yellowish crude acyl chloride product; S1-2. Under argon protection and 0-5°C, sodium hydride is dissolved in dry tetrahydrofuran; then, a dry tetrahydrofuran solution containing (R)-4-isopropyloxazolidin-2-one is slowly added; then, the temperature is raised to 25-30°C, and stirred for 2-4 hours; then, the temperature is lowered to 0-5°C, a dry tetrahydrofuran solution containing a crude acid chloride solution is slowly added, and stirred at room temperature for 4-6 hours; then, the mixture is quenched, separated, extracted, washed, dried and concentrated, and finally purified by silica gel column chromatography to obtain (R)-3-(5-hexenoyl)-4-isopropyloxazolidin-2-one.

[0007] Preferably, in step S1-1, the molar ratio of oxalyl chloride, dimethylformamide and 5-hexenoic acid is (1.5-2.0):(0.01-0.02):(1.0-1.3); the dichloromethane solution containing 5-hexenoic acid is obtained by uniformly mixing 5-hexenoic acid and dichloromethane in a mass ratio of (1.0-1.3):(1.5-2).

[0008] Preferably, in step S1-2, the molar ratio of sodium hydride to (R)-4-isopropyloxazolidin-2-one is (1.3-1.5):(1.1-1.2); the mass ratio of sodium hydride to dry tetrahydrofuran is (1.3-1.5):(25-30); the dry tetrahydrofuran solution containing (R)-4-isopropyloxazolidin-2-one is obtained by uniformly mixing (R)-4-isopropyloxazolidin-2-one and dry tetrahydrofuran in a mass ratio of (1.1-1.2):(5-6), and the dry tetrahydrofuran solution containing the crude acid chloride solution is obtained by uniformly mixing the crude acid chloride solution and dry tetrahydrofuran in a mass ratio of (1.0-1.1):(5-6).

[0009] Preferably, step S2 includes the following specific steps: Under the protection of argon and at -78 to -80°C, (R)-3-(5-hexenoyl)-4-isopropyloxazolidin-2-one is dissolved in dry tetrahydrofuran, and then sodium hexamethyldisilazide is slowly added at a rate of 20 to 25 ml / h. After stirring for 1 to 1.5 hours, iodomethane is added dropwise; then, the mixture is stirred at -78 to -80°C for 2 to 2.5 hours, and then the temperature is raised to -60 to -50°C for reaction for 3 to 5 hours; then, the mixture is quenched, separated, extracted, washed, dried and concentrated, and finally purified by silica gel column chromatography to obtain (R)-4-isopropyl-3-((R)-2-methyl-5-hexenoyl)oxazolidin-2-one.

[0010] Preferably, in step S2, the molar ratio of (R)-3-(5-hexenoyl)-4-isopropyloxazolidine to sodium hexamethyldisilazide is (1.0-1.1):(1.5-1.8), the molar ratio of sodium hexamethyldisilazide to methyl iodide is (1.5-1.8):(5-6), and the mass ratio of (R)-3-(5-hexenoyl)-4-isopropyloxazolidine to dry tetrahydrofuran is (1.0-1.1):(10-11).

[0011] A (S)-5-methylundecene, wherein the (S)-5-methylundecene is synthesized by using (R)-4-isopropyl-3-((R)-2-methyl-5-hexenoyl)oxazolidin-2-one as a raw material, and the (R)-4-isopropyl-3-((R)-2-methyl-5-hexenoyl)oxazolidin-2-one is the above-mentioned (R)-4-isopropyl-3-((R)-2-methyl-5-hexenoyl)oxazolidin-2-one.

[0012] A method for synthesizing (S)-5-methylundecene, wherein the (S)-5-methylundecene is the (S)-5-methylundecene according to claim 4; the method for synthesizing (S)-5-methylundecene comprises the following steps: 1) Reducing (R)-4-isopropyl-3-((R)-2-methyl-5-hexenoyl)oxazolidin-2-one by LiAlH4 to obtain (R)-2-methyl-5-hexen-1-ol; 2) (R)-2-methyl-5-hexen-1-ol is activated by reaction with TsCl, and then coupled with amylmagnesium bromide under the catalysis of Li2CuCl4 to prepare (S)-5-methylundecene; The (R)-4-isopropyl-3-((R)-2-methyl-5-hexenoyl)oxazolidin-2-one is the above-mentioned (R)-4-isopropyl-3-((R)-2-methyl-5-hexenoyl)oxazolidin-2-one.

[0013] Preferably, step 1) specifically includes the following steps: Under argon protection and 0°C to -5°C, LiAlH4 is dissolved in dry tetrahydrofuran, and then a dry tetrahydrofuran solution of (R)-4-isopropyl-3-((R)-2-methyl-5-hexenoyl)oxazolidin-2-one is slowly added dropwise at a dropping rate of 30 to 35 ml / h. Then, the temperature is raised to 25 to 30°C and stirred for 12 to 16 hours, followed by quenching, dilution, suction filtration, drying and concentration, and finally purification by silica gel column chromatography to obtain (R)-2-methyl-5-hexen-1-ol.

[0014] Preferably, step 2) specifically includes the following steps: 2-1), under the protection of argon, p-toluenesulfonyl chloride is slowly added to a dry dichloromethane solution containing (R)-2-methyl-5-hexen-1-ol and triethylamine; then, stirred at room temperature for 18 hours; then quenched, separated, extracted, washed, dried and concentrated to obtain a crude p-toluenesulfonate in the form of a colorless oil; 2-2), under the protection of argon and at -20°C to -25°C, add Li2CuCl4 to a dry tetrahydrofuran solution of the crude p-toluenesulfonate, and then slowly add amylmagnesium bromide, and then warm to room temperature and stir overnight; then quench, separate, extract, wash, dry and concentrate, and purify by silica gel column chromatography to obtain (S)-5-methylundecene.

[0015] Preferably, in step 1), the molar ratio of (R)-4-isopropyl-3-((R)-2-methyl-5-hexenoyl)oxazolidin-2-one to LiAlH4 is (1.0-1.1):(3.5-3.8), the dry tetrahydrofuran solution containing (R)-4-isopropyl-3-((R)-2-methyl-5-hexenoyl)oxazolidin-2-one is obtained by uniformly mixing (R)-4-isopropyl-3-((R)-2-methyl-5-hexenoyl)oxazolidin-2-one and dry tetrahydrofuran in a mass ratio of (1.0-1.1):(5-5.5), and the mass ratio of LiAlH4 to dry tetrahydrofuran is (3.5-3.8):(30-33).

[0016] Preferably, in step 2-1), the dry dichloromethane solution containing (R)-2-methyl-5-hexen-1-ol and triethylamine is obtained by uniformly mixing (R)-2-methyl-5-hexen-1-ol, triethylamine and dry dichloromethane in a molar ratio of (1.0-1.1):(1.75-2.0):(30-33), and the molar ratio of triethylamine to p-toluenesulfonyl chloride is (1.75-2.0):(2.0-2.3).

[0017] Preferably, in step 2-2), the molar ratio of the crude p-toluenesulfonate, Li2CuCl4 and amylmagnesium bromide is (1.0-1.1):(0.1-0.12):(3.0-3.6), and the dry tetrahydrofuran solution of the crude p-toluenesulfonate is obtained by uniformly mixing the crude p-toluenesulfonate with dry tetrahydrofuran in a mass ratio of (1.0-1.1):(10-11). The Li2CuCl4 and hexylmagnesium bromide used in this application are both existing reagents, the specification of Li2CuCl4 is (0.1M, solution in THF), and the specification of hexylmagnesium bromide is (1.0M, in THF).

[0018] Disclosed is 1-(((5R,11S)-5,11-dimethylheptadecen-1-yl)-6-sulfonyl)-4-methylbenzene, wherein the 1-(((5R,11S)-5,11-dimethylheptadecen-1-yl)-6-sulfonyl)-4-methylbenzene is prepared by using (S)-5-methylundecene as a raw material, and the (S)-5-methylundecene is the above-mentioned (S)-5-methylundecene.

[0019] A method for synthesizing 1-(((5R,11S)-5,11-dimethylheptadecene-1-yl)-6-sulfonyl)-4-methylbenzene, wherein the 1-(((5R,11S)-5,11-dimethylheptadecene-1-yl)-6-sulfonyl)-4-methylbenzene is the above-mentioned 1-(((5R,11S)-5,11-dimethylheptadecene-1-yl)-6-sulfonyl)-4-methylbenzene; the method for synthesizing 1-(((5R,11S)-5,11-dimethylheptadecene-1-yl)-6-sulfonyl)-4-methylbenzene comprises the following steps: A. subjecting (S)-5-methylundecene to a hydroboration oxidation reaction to synthesize (S)-5-methylundecyl alcohol, and then subjecting (S)-5-methylundecyl alcohol to an iodination reaction to synthesize a chiral intermediate (S)-1-iodo-5-methylundecane; the (S)-5-methylundecyl alcohol is the above-mentioned (S)-5-methylundecyl alcohol; B. (R)-2-methyl-5-hexen-1-ol is used for iodination reaction to synthesize (R)-6-iodo-5-methyl-1-hexene, and then (R)-6-iodo-5-methyl-1-hexene is reacted with p-Me(C6H4)SO2Na to synthesize (R)-1-methyl-4-((2-methyl-5-hexenyl)sulfonyl)benzene, and then (R)-1-methyl-4-((2-methyl-5-hexenyl)sulfonyl)benzene is alkylated with chiral intermediate (S)-1-iodo-5-methylundecane to synthesize 1-(((5R,11S)-5,11-dimethylheptadecen-1-yl)-6-sulfonyl)-4-methylbenzene.

[0020] Preferably, step A) specifically comprises the following steps: Under argon protection, 9-boranebicyclo[3.3.1]nonene is slowly added to a dry tetrahydrofuran solution of (S)-5-methylundecene; after stirring at room temperature for 12 to 16 hours, the temperature is lowered to 0 to 5°C, and then a sodium hydroxide solution is added, and stirred for 30 minutes; after cooling to -20°C, a hydrogen peroxide solution is slowly added; then, the mixture is stirred at room temperature for 3 hours, quenched, separated, extracted, washed, dried and concentrated, and purified by silica gel column chromatography to obtain (S)-5-methylundecyl alcohol; Under argon protection, (S)-5-methylundecanol, triphenylphosphine and imidazole are added to dry tetrahydrofuran and stirred evenly, and then a dry tetrahydrofuran solution of iodine is slowly added; after stirring for 3 to 5 hours, quenching, separation, extraction, washing, drying and concentration are performed, and (S)-1-iodo-5-methylundecane is obtained after purification by silica gel column chromatography.

[0021] Preferably, in step A), the molar ratio of (S)-5-methylundecene, 9-borabicyclo[3.3.1]nonene and sodium hydroxide is (1.0-1.1):(3.0-3.5):(6-7); the dry tetrahydrofuran solution of (S)-5-methylundecene is obtained by uniformly mixing (S)-5-methylundecene and dry tetrahydrofuran solution in a mass ratio of (1.0-1.1):(15-17), the molar ratio of sodium hydroxide to hydrogen peroxide is (6-7):(18-21), the molar concentration of the sodium hydroxide solution is 3-3.5M, and the mass percentage of the hydrogen peroxide solution is 30%-35%; Among them, the molar ratio of (S)-5-methylundecanol, triphenylphosphine and imidazole is (1.0-1.1):(1.2-1.5):(2-3), the molar ratio of iodine element and imidazole is (1.2-1.5):(2-3), and the mass ratio of (S)-5-methylundecanol and dry tetrahydrofuran is (1.0-1.1):(11-15).

[0022] Preferably, step B) specifically comprises the following steps: under the protection of argon, adding (R)-2-methyl-5-hexen-1-ol, triphenylphosphine and imidazole to dry tetrahydrofuran and stirring evenly, slowly adding a dry tetrahydrofuran solution of iodine; after stirring for 3 to 5 hours, quenching, separating, extracting, washing, drying and concentrating, and purifying by silica gel column chromatography to obtain (R)-6-iodo-5-methyl-1-hexene; Under argon protection, sodium p-toluenesulfinate, polyethylene glycol-400 (PEG-400) and dimethyl sulfoxide (DMSO) are mixed and stirred evenly, and (R)-6-iodo-5-methyl-1-hexene is slowly added; then, the mixture is heated to 80-85° C. and stirred for 2-3 hours; after cooling to room temperature, the mixture is quenched, separated, extracted, washed, dried and concentrated, and purified by silica gel column chromatography to obtain (R)-1-methyl-4-((2-methyl-5-hexenyl)sulfonyl)benzene; Under the protection of argon and at -78 to -80°C, (R)-1-methyl-4-((2-methyl-5-hexenyl)sulfonyl)benzene is dissolved in dry tetrahydrofuran, and n-butyl lithium n-BuLi is slowly added; the mixture is stirred at -78°C for 30 minutes, and then the temperature is raised to -35 to -30°C and stirred for 30 to 40 minutes; then the mixture is cooled to -78 to -80°C, and then a mixed solution of hexamethylphosphoramide HMPA, dry tetrahydrofuran and (S)-1-iodo-5-methylundecane is slowly added, and then the temperature is raised to room temperature and stirred overnight; then the mixture is quenched, separated, extracted, washed, dried and concentrated, and purified by silica gel column chromatography to obtain 1-(((5R,11S)-5,11-dimethylheptadecen-1-yl)-6-sulfonyl)-4-methylbenzene.

[0023] Preferably, in step B), the molar ratio of (R)-2-methyl-5-hexen-1-ol, triphenylphosphine and imidazole is (1.0-1.1):(1.2-1.5):(2-3), the molar ratio of iodine to imidazole is (1.2-1.5):(2-3), the mass ratio of (R)-2-methyl-5-hexen-1-ol to dry tetrahydrofuran is (1.0-1.1):(11-15); (R)-6-iodo-5-methyl-1-hexene, sodium p-toluenesulfinate, polyethylene glycol-400 and The molar ratios of dimethyl sulfoxide (DMSO) are (1.0-1.1):(1.4-1.6):(17-20):(8-10); the molar ratios of (R)-1-methyl-4-((2-methyl-5-hexenyl)sulfonyl)benzene, n-butyl lithium n-BuLi, (S)-1-iodo-5-methylundecane, phosphamide HMPA and dry tetrahydrofuran are (1.0-1.1):(1.5-1.8):(1.2-1.5):(4.8-6):(15-18).

[0024] A (5R, 11S)-5,11-dimethylheptadecane, wherein the structural formula of the (5R, 11S)-5,11-dimethylheptadecane is as shown in Formula 1:

[0025] The (5R, 11S)-5,11-dimethylheptadecane is prepared by using 1-(((5R, 11S)-5,11-dimethylheptadecane-1-yl)-6-sulfonyl)-4-methylbenzene; the 1-(((5R, 11S)-5,11-dimethylheptadecane-1-yl)-6-sulfonyl)-4-methylbenzene is the above-mentioned 1-(((5R, 11S)-5,11-dimethylheptadecane-1-yl)-6-sulfonyl)-4-methylbenzene; the (5R, 11S)-5,11-dimethylheptadecane is a component of the sex pheromone of the western hemlock looper.

[0026] A method for preparing (5R, 11S)-5,11-dimethylheptadecane, wherein the (5R, 11S)-5,11-dimethylheptadecane is the above-mentioned (5R, 11S)-5,11-dimethylheptadecane; the method for preparing (5R, 11S)-5,11-dimethylheptadecane comprises the following steps: (1) removing the sulfonyl group from 1-(((5R,11S)-5,11-dimethylheptadecen-1-yl)-6-sulfonyl)-4-methylbenzene by treating it with activated Mg / MeOH; (2) Reduction with Pd / C catalyst to synthesize (5R,11S)-5,11-dimethylheptadecane.

[0027] Preferably, step (1) specifically comprises the following steps: Under argon protection, magnesium powder is dissolved in dry tetrahydrofuran, and then MeMgBr is added; after stirring at room temperature for 15 to 20 minutes, a dry methanol solution of 1-(((5R,11S)-5,11-dimethylheptadecen-1-yl)-6-sulfonyl)-4-methylbenzene is slowly added, and then stirred at 50 to 55° C. for 4 to 6 hours; then, quenching, separation, extraction, washing, drying and concentration are performed to obtain a crude product of (5S,11S)-5,11-dimethylheptadecen-1-ene.

[0028] Preferably, in step (1), the mass ratio of 1-(((5R,11S)-5,11-dimethylheptadecen-1-yl)-6-sulfonyl)-4-methylbenzene to magnesium powder is (1.0-1.1):(1.2-1.5), the mass ratio of magnesium powder to dry tetrahydrofuran is (1.2-1.5):(10-15), and the molar ratio of MeMgBr to magnesium powder is (0.02-0.03):(1 .2~1.5), the dry methanol solution containing 1-(((5R,11S)-5,11-dimethylheptadecen-1-yl)-6-sulfonyl)-4-methylbenzene is obtained by uniformly mixing 1-(((5R,11S)-5,11-dimethylheptadecen-1-yl)-6-sulfonyl)-4-methylbenzene and MeOH in a mass ratio of (1.0~1.1):(30~35).

[0029] Preferably, step (2) specifically comprises the following steps: Under the protection of hydrogen, a methanol solution of the crude product of (5S,11S)-5,11-dimethylheptadecan-1-ene is added to a methanol suspension containing palladium carbon, and the methanol suspension of palladium carbon is the Pd / C catalyst; the mixture is stirred at 25 to 30° C. for 12 to 15 hours and concentrated in vacuo; and (5R,11S)-5,11-dimethylheptadecane is obtained after purification by silica gel column chromatography.

[0030] Preferably, in step (2), the mass ratio of 1-(((5R,11S)-5,11-dimethylheptadecen-1-yl)-6-sulfonyl)-4-methylbenzene to palladium carbon is (1.0-1.1):(0.2-0.3); the methanol suspension of palladium carbon is obtained by uniformly mixing palladium carbon and methanol in a mass ratio of (0.2-0.3):(8-10).

[0031] A (S)-7-methylheptadecane, wherein the structural formula of the (S)-7-methylheptadecane is as shown in Formula 2: The (S)-7-methylheptadecane is prepared by using (S)-5-methylundecyl alcohol as a raw material; the (S)-5-methylundecyl alcohol is the above-mentioned (S)-5-methylundecyl alcohol; the (S)-7-methylheptadecane is another component of the western hemlock looper sex pheromone.

[0032] A method for preparing (S)-7-methylheptadecane, wherein the (S)-7-methylheptadecane is the above-mentioned (S)-7-methylheptadecane; the method for preparing (S)-7-methylheptadecane comprises the following steps: a), activating (S)-5-methylundecanol by reaction with TsCl; b) Coupled with hexylmagnesium bromide to synthesize (S)-7-methylheptadecane.

[0033] Preferably, step a) specifically comprises the following steps: Under argon protection, p-toluenesulfonyl chloride is slowly added to a dichloromethane solution containing (S)-5-methylheptadecanol and triethylamine, and stirred at room temperature for 18 to 20 hours; then, quenching, separation, extraction, washing, drying and concentration are performed, and p-toluenesulfonate product is obtained after purification by silica gel column chromatography.

[0034] Preferably, in step a), the molar ratio of triethylamine to p-toluenesulfonyl chloride is (1.75-2.0):(2.0-2.3); and the dichloromethane solution containing (S)-5-methylheptadecanol and triethylamine is obtained by uniformly mixing (S)-5-methylheptadecanol, triethylamine and dichloromethane, wherein the molar ratio of (S)-5-methylheptadecanol to triethylamine is (1.0-1.1):(1.75-2.0), and the mass ratio of (S)-5-methylheptadecanol to dichloromethane is (1.0-1.1):(30-33); Preferably, step b) specifically comprises the following steps: Under argon protection and at -20°C, Li2CuCl4 and hexylmagnesium bromide are added to a dry tetrahydrofuran solution of p-toluenesulfonate; then, the temperature is gradually raised to room temperature and stirred at room temperature overnight; then, quenching, separation, extraction, washing, drying and concentration are performed, and (S)-7-methylheptadecane is obtained after purification by silica gel column chromatography.

[0035] Preferably, in step b), the molar ratio of p-toluenesulfonate to Li2CuCl4 is (1.0-1.1):(0.1-0.12), the molar ratio of Li2CuCl4 to hexylmagnesium bromide is (0.1-0.12):(3.0-3.6), and the dry tetrahydrofuran solution of p-toluenesulfonate is obtained by uniformly mixing p-toluenesulfonate with dry tetrahydrofuran in a mass ratio of (1.0-1.1):(10-11); Li2CuCl4 and hexylmagnesium bromide used in the present application are both existing reagents, the specification of Li2CuCl4 is (0.1M, solution in THF), and the specification of hexylmagnesium bromide is (1.0M, in THF).

[0036] A method for synthesizing (5R, 11S)-5,11-dimethylheptadecane (i.e., component 1 of the western hemlock looper sex pheromone), comprising the following steps: Firstly, (S)-5-methylundecene was synthesized using (R)-4-isopropyl-3-((R)-2-methyl-5-hexenoyl)oxazolidin-2-one as a raw material; Then, 1-(((5R,11S)-5,11-dimethylheptadecen-1-yl)-6-sulfonyl)-4-methylbenzene was synthesized using (S)-5-methylundecene as a raw material; Finally, (5R,11S)-5,11-dimethylheptadecane (i.e., component 1 of the sex pheromone of the western hemlock looper) was synthesized using 1-(((5R,11S)-5,11-dimethylheptadecen-1-yl)-6-sulfonyl)-4-methylbenzene as raw material.

[0037] A method for synthesizing (S)-7-methylheptadecane (i.e., component 2 of the sex pheromone of western hemlock looper) comprises the following steps: Firstly, (S)-5-methylundecene was synthesized using (R)-4-isopropyl-3-((R)-2-methyl-5-hexenoyl)oxazolidin-2-one as a raw material; Then, (S)-5-methylundecene is used as a raw material to synthesize (S)-5-methylundecanol; Finally, (S)-7-methylheptadecane (i.e., component 2 of the sex pheromone of the western hemlock looper) was synthesized using (S)-5-methylundecanol as a raw material.

[0038] Compared with the prior art, the beneficial technical effects of this application are: (1) The present application provides a novel method for synthesizing (R)-4-isopropyl-3-((R)-2-methyl-5-hexenoyl)oxazolidin-2-one. The optical purity of the (R)-4-isopropyl-3-((R)-2-methyl-5-hexenoyl)oxazolidin-2-one synthesized in the present application is greater than 99%, and the synthesis yield is as high as 68%; The present application uses (R)-4-isopropyl-3-((R)-2-methyl-5-hexenoyl)oxazolidin-2-one to synthesize component 1 (i.e., (5R, 11S)-5,11-dimethylheptadecane) of the sex pheromone of the western hemlock looper, with a total yield of up to 18%, and the optical purity of the synthesized (5R, 11S)-5,11-dimethylheptadecane is greater than 99%; The present application utilizes (R)-4-isopropyl-3-((R)-2-methyl-5-hexenoyl)oxazolidin-2-one to synthesize component 2 (i.e., (S)-7-methylheptadecane) of the sex pheromone of the western hemlock looper, with a total yield of up to 30%, and the optical purity of the synthesized (5R, 11S)-5,11-dimethylheptadecane is greater than 99%. BRIEF DESCRIPTION OF THE DRAWINGS

[0039] Figure 1 The result of nuclear magnetic resonance hydrogen spectrum test of (R)-2-methylhex-5-en-1-yl (R)-3,3,3-trifluoro-2-methoxy-2-phenylpropionate was obtained. 1 H NMR spectrum. DETAILED DESCRIPTION

[0040] Embodiment 1: The synthesis method of (R)-4-isopropyl-3-((R)-2-methyl-5-hexenoyl)oxazolidin-2-one (as shown in Formula 7) is shown in the following reaction formula: The synthesis method of (R)-4-isopropyl-3-((R)-2-methyl-5-hexenoyl)oxazolidin-2-one (as shown in Formula 7) specifically comprises the following steps: S1. Under argon protection, 5-hexenoic acid (1.72 g, 15 mmol) was dissolved in 20 ml of dry dichloromethane (DCM) to obtain a dichloromethane solution containing 5-hexenoic acid. The structural formula of 5-hexenoic acid is shown in Formula 4. Then, the temperature was adjusted to 0°C. Then, oxalyl chloride (2.86 g, 22.5 mmol) and 0.1 ml of dimethylformamide (DMF) were slowly added, and then stirred at 0°C for 2 hours. Then, the solvent was removed by concentration under reduced pressure to obtain a slightly yellowish crude acyl chloride product. Under argon protection and 0°C, sodium hydride (0.9 g, 22.5 mmol) was dissolved in 20 ml of dry tetrahydrofuran. Sodium hydride is a commercial reagent with the specification of: NaH 60% is dispersed in mineral oil; then, a dry tetrahydrofuran solution containing (R)-4-isopropyloxazolidin-2-one is slowly added to obtain a reaction solution, wherein the structural formula of (R)-4-isopropyloxazolidin-2-one is shown in Formula 5, and the dry tetrahydrofuran solution of (R)-4-isopropyloxazolidin-2-one is obtained by uniformly mixing (R)-4-isopropyloxazolidin-2-one (3.46 g, 19.5 mmol) and 20 ml of dry tetrahydrofuran; then, the reaction solution is heated to 25° C. and stirred for 2 hours; then, the temperature is lowered to 0° C., a slightly yellowish crude acid chloride product is dissolved in 10 ml of tetrahydrofuran to obtain a dry tetrahydrofuran solution containing the crude acid chloride product, and the dry tetrahydrofuran solution containing the crude acid chloride product is slowly dripped into to the reaction solution, and then stirred at room temperature for 4 hours; then, quenching the reaction with a saturated aqueous solution of ammonium chloride (20 ml) to obtain a reaction mass, and after the reaction mass is layered, an aqueous phase is obtained to complete the separation process, and the aqueous phase is extracted with ethyl acetate for 3 times to obtain three organic phase samples, and the amount of ethyl acetate used in each extraction process is 50 ml; then, the three organic phase samples are mixed, and the mixed organic phase is washed with brine (50 ml), and then dried over anhydrous sodium sulfate, and concentrated under reduced pressure; the residue after reduced pressure concentration is purified by silica gel column chromatography (ethyl acetate / petroleum ether=1:5) to obtain (R)-3-(5-hexenoyl)-4-isopropyloxazolidin-2-one (as shown in Formula 6), which is a light yellow oil (3.04 g, yield 90%); The specific rotation, H NMR, C NMR and high resolution mass spectrometry of (R)-3-(5-hexenoyl)-4-isopropyloxazolidin-2-one were measured. The results are as follows: [α] D 25 = -67.66 (c 1.80, CHCl3); 1H NMR(400MHz,Chloroform-d)δ5.85–5.75(m,1H),5.12–4.94(m,2H),4.45–4.41(m 1H),4.30–4.17(m,2H),3.03–2.84(m,2H),2.41–2.33(m,1H),2.13(q,J=7 .2Hz,2H),1.83–1.71(m,2H),0.91(d,J=7.0Hz,3H),0.87(d,J=6.9Hz,3H); 13 C NMR(101MHz, CDCl3)δ173.20,154.14,137.91,115.36,63.42,58.45,34.90,33.11,28.46,23.63,18.04,14.73; HRMS(ESI,m / z):calculated for[M+Na] + C 12 H 19 NO3Na 248.1257, found: 248.1240.

[0041] S2. Under argon protection and -78°C, (R)-3-(5-hexenoyl)-4-isopropyloxazolidin-2-one (3.38 g, 15 mmol) was dissolved in dry tetrahydrofuran (40 ml). The structural formula of (R)-3-(5-hexenoyl)-4-isopropyloxazolidin-2-one is shown in Formula 6. Then, sodium hexamethyldisilazide (NaHMDS, 11.25 ml, 2.0 M in THF, 22.5 mmol) was slowly added at a rate of 20 ml / h. Sodium hexamethyldisilazide was an existing reagent. After stirring for 1 hour, iodomethane (MeI, 4.67 ml, 75 mmol) was added dropwise. Then, the mixture was heated at -78°C. ℃ temperature, stirred for 2 hours, and then heated to -60℃ for reaction for 3 hours; then, quenched the reaction with saturated aqueous ammonium chloride solution (30ml) to obtain a reaction mass; after the reaction mass was layered, an aqueous phase was obtained, and the liquid separation process was completed. The aqueous phase was extracted with ethyl acetate 3 times, and the amount of ethyl acetate used in each extraction process was 50ml; the mixed organic phase was washed with brine (50ml), dried over anhydrous sodium sulfate, and concentrated under reduced pressure; the residue was purified by silica gel column chromatography (ethyl acetate / petroleum ether=1:8) to obtain (R)-4-isopropyl-3-((R)-2-methyl-5-hexenoyl)oxazolidin-2-one (as shown in Formula 7) in the form of a colorless oil (2.73g, yield 76%); The specific rotation, H NMR, C NMR and high resolution mass spectrometry of (R)-4-isopropyl-3-((R)-2-methyl-5-hexenoyl)oxazolidin-2-one were measured, and the results were as follows: [α]D 25 = -91.08 (c 0.55, CHCl3); 1 H NMR(400MHz,Chloroform-d)δ5.83–5.73(m,1H),5.03–4.89(m,2H),4.46–4.42(m,1H),4.28–4.18(m,2H),3.80–3.71(m,1H),2.38–2.31 (m,1H),2.06(q,J=7.1Hz,2H),1.90–1.81(m,1H),1.52–1.45(m,1H),1.21(d,J=6.9Hz,3H),0.91(d,J=7.0Hz,3H),0.87(d,J=6.9Hz,3H); 13 C NMR (101MHz, CDCl3) δ177.17,153.78,138.30,114.99,63.37,58.57,37.34,32.30,31.68,28.60,18.08,18.06,14.85; HRMS (ESI, m / z): calculated for [M+Na] + C 13 H 21 NO3Na 262.1414, found: 262.1417.

[0042] Embodiment 2: The preparation method of (S)-5-methylundecene (as shown in Formula 10) has a synthetic route as shown in the following reaction formula: The preparation method of (S)-5-methylundecene (as shown in Formula 10) specifically comprises the following steps: 1) Under argon protection and 0°C, LiAlH4 (1.50 g, 38.75 mmol) was dissolved in 15 ml of dry tetrahydrofuran to obtain a mixture; then (R)-4-isopropyl-3-((R)-2-methyl-5-hexenoyl)oxazolidin-2-one (2.65 g, 11.07 mmol) (as shown in Formula 7) was dissolved in 15 ml of dry tetrahydrofuran, and then slowly dripped into the mixture at a dripping speed of 30 ml / h for 20 minutes; then The mixture was heated to 25° C. and stirred for 12 hours, and then saturated aqueous ammonium chloride solution (20 ml) was slowly added to quench the mixture, and the mixture was diluted with ethyl acetate; the mixture was then filtered to remove the precipitate, and the filtrate was dried over anhydrous sodium sulfate and then filtered to obtain a filtrate; the filtrate was concentrated under reduced pressure, and the residue after concentration under reduced pressure was purified by silica gel column chromatography (ethyl acetate / petroleum ether=1:5) to obtain (R)-2-methyl-5-hexen-1-ol (as shown in Formula 8) in the form of a colorless oil (1.09 g, yield 86%, ≥99% ee); The optical purity of the Moschel ester derived from (R)-2-methyl-5-hexen-1-ol was determined by NMR; The specific rotation, nuclear magnetic resonance hydrogen spectrum, carbon spectrum and high-resolution mass spectrometry of (R)-2-methyl-5-hexen-1-ol were measured, and the results were as follows: [α] D 25 = +7.17 (c 0.61, CHCl3); 1 H NMR(400MHz,Chloroform-d)δ5.86–5.76(m,1H),4.98(dd,J=27.7,13.6Hz,2H),3.53–3.41(m,2H),2.18– 2.00(m,2H),1.70–1.59(m,1H),1.56–1.47(m,1H),1.41(s,1H),1.25–1.16(m,1H),0.93(d,J=6.7Hz,3H); 13 C NMR(101MHz, CDCl3)δ139.03,114.54,68.31,35.35,32.43,31.31,16.57; HRMS(ESI,m / z):calculated for[M+K] + C7H 14 OK 153.0676, found:153.0662.

[0043] 2) Under argon protection, a dry dichloromethane solution of (R)-2-methyl-5-hexene-1-ol (as shown in Formula 8) and triethylamine was slowly added to a dry dichloromethane solution of p-toluenesulfonyl chloride, wherein the dry dichloromethane solution of p-toluenesulfonyl chloride was obtained by uniformly mixing p-toluenesulfonyl chloride (1.90 g, 10.0 mmol) and 20 ml of dry methyl chloride, and the dry dichloromethane solution of (R)-2-methyl-5-hexene-1-ol (as shown in Formula 8) and triethylamine was obtained by mixing (R)-2-methyl-5-hexene-1-ol (0.57 g, 5.0 mmol) and triethylamine (1.24 mL, 8.75 mmol) and 10ml of dry dichloromethane were mixed uniformly; then, stirred at room temperature for 18 hours; then, quenched with saturated sodium bicarbonate aqueous solution (20mL), the reaction materials were separated to obtain an aqueous phase, the liquid separation process was completed, and then extracted with dichloromethane 3 times to obtain three organic phase samples, and the amount of dichloromethane used in each extraction process was 30mL; after mixing the three organic phase samples, the mixed organic phase samples were washed with brine (30mL), then dried over anhydrous sodium sulfate, and concentrated under reduced pressure; the residue after reduced pressure concentration was purified by silica gel column chromatography (ethyl acetate / petroleum ether=1:5) to obtain a crude p-toluenesulfonate product in the form of a colorless oil; Under argon protection and -20 ° C, Li2CuCl4 (5.0 mL, 0.5 mmol) was added to the dry tetrahydrofuran solution of the crude p-toluenesulfonate product, wherein the dry tetrahydrofuran solution of the crude p-toluenesulfonate product was obtained by uniformly mixing the crude p-toluenesulfonate product (5.0 mmol, 1.0 equivalent) and 10 ml of dry tetrahydrofuran (10 mL). The Li2CuCl4 used in this application is an existing reagent, and the specification of Li2CuCl4 is (0.1 M, solution in THF); then pentylmagnesium bromide (as shown in Formula 9, 15.0 mL, 15.0 mmol) was slowly added. The pentylmagnesium bromide used in this application is an existing reagent, and its specification is (1.0 M, in THF), warmed to room temperature and stirred overnight; then quenched with saturated aqueous ammonium chloride solution (30 mL), after the reaction was completed, the reaction materials were separated to obtain an aqueous phase, and the separation process was completed. The aqueous phase was extracted with ethyl acetate three times to obtain three organic phase samples, and the amount of ethyl acetate used in each extraction process was 40 mL; the organic phase samples were mixed, and the mixed organic phases were washed with brine (40 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure; the residue after reduced pressure concentration was purified by silica gel column chromatography (petroleum ether) to obtain (S)-5-methylundecene (as shown in Formula 10, 0.70 g, yield 83%), which was a colorless oil; The specific rotation, nuclear magnetic resonance hydrogen spectrum, carbon spectrum and high-resolution mass spectrometry of (S)-5-methylundecene were measured, and the results were as follows: [α]D 25 = -1.22 (c 0.65, CHCl3); 1 H NMR(400MHz,Chloroform-d)δ5.87–5.77(m,1H),5.05–4.90(m,2H),2.13–1.98(m ,2H),1.44–1.36(m,2H),1.31–1.24(m,9H),1.21–1.07(m,2H),0.90–0.85(m,6H); 13 C NMR (101MHz, CDCl3) δ139.65,114.06,37.11,36.40,32.44,32.10,31.55,29.83,27.13,22.85,19.68,14.28; HRMS (ESI, m / z): calculated for [M+Na] + C 12 H 24 Na 191.1770, found:191.1786.

[0044] In the present application, (R)-4-isopropyl-3-((R)-2-methyl-5-hexenoyl)oxazolidin-2-one (as shown in Formula 7) contains two chiral centers, and its ee (enantiomeric excess) value cannot be directly determined. In order to determine the optical purity of the compound, the present application is based on the Mosher esterification derivatization of (R)-2-methyl-5-hexen-1-ol (as shown in Formula 8) and then optical testing. (R)-2-methyl-5-hexen-1-ol is derived from (R)-4-isopropyl-3- The results of optical testing after (R)-2-methyl-5-hexen-1-ol was subjected to Mosher esterification and then converted from ((R)-2-methyl-5-hexenoyl)oxazolidin-2-one by reduction reaction can prove the optical purity of (R)-4-isopropyl-3-((R)-2-methyl-5-hexenoyl)oxazolidin-2-one (as shown in Formula 7); wherein the reaction path of (R)-2-methyl-5-hexen-1-ol by Mosher esterification is as follows: The reaction of the Mosher esterification derivatization of (R)-2-methyl-5-hexen-1-ol comprises the following steps: under the protection of argon and at 0°C, 4-dimethylaminopyridine (DMAP, 12.2 mg, 0.1 mmol, 1.0 equiv.) and triethylamine (50.6 mg, 0.5 mmol, 5.0 equiv.) are dissolved in 4 ml of dichloromethane, and then (R)-2-methyl-5-hexen-1-ol (as shown in Formula 8, 11.4 mg, 0.1 mmol, 1.0 equiv.) is added dropwise, stirred for 10 minutes, and then (S)-(-)-α-methoxy-α-(trifluoromethyl)phenylacetyl chloride (50.6 mg , 0.2mmol, 2.0equiv.), and then stirred at room temperature for 12 hours; then, quenched with water (3mL), and then extracted with dichloromethane three times to obtain three organic phase samples, and the amount of dichloromethane used in each extraction process was 10mL; after mixing the three organic phase samples, the mixed organic phase sample was washed with brine (20mL), and then dried over anhydrous sodium sulfate and concentrated under reduced pressure; the residue after reduced pressure concentration was purified by preparative chromatography to obtain (R)-2-methylhex-5-en-1-yl (R)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate (as shown in Formula 23, 21.8mg, yield 66%) as a colorless oil.

[0045] The (R)-2-methylhex-5-en-1-yl (R)-3,3,3-trifluoro-2-methoxy-2-phenylpropionate (as shown in Formula 23) was tested by H NMR to obtain Figure 1 shown 1 H NMR spectrum. 1 From the H NMR spectrum we can see: 1 HNMR(400MHz,Chloroform-d)δ7.53–7.51(m,2H),7.41–7.40(m,3H),5.80–5.70(m,1H),5.02–4.94(m,2H),4.24(dd,J=10.7,5.6Hz,1H),4. 10(dd,J=10.7,6.5Hz,1H),3.55(s,3H),2.14–1.99(m,2H),1.92–1.84(m,1H),1.51–1.42(m,1H),1.31–1.22(m,1H),0.93(d,J=6.8Hz,3H). HRMS(ESI,m / z):calculated for[M+H] + C 17 H 22 F3O3331.1510,found:331.1516.

[0046] from Figure 1 It can be seen that (R)-2-methylhex-5-en-1-yl (R)-3,3,3-trifluoro-2-methoxy-2-phenylpropionate (as shown in Formula 23) 1 The chemical shift at 3.551 in the H NMR spectrum is the methoxy group. 1 The H NMR spectrum shows only one single peak at the chemical shift of 3.551, and no other single peaks are observed at this position, which proves that the compound is a single isomer without other diastereomers. At the same time, the chemical shift of 0.93 is the chiral methyl in the structure. Only one double peak is observed at the chemical shift of 0.93, and no other double peaks are observed at this position. This spectrum proves that the optical purity of (R)-2-methylhex-5-en-1-yl (R)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate (as shown in Formula 23) is greater than 99%. -2-methoxy-2-phenylpropanoate is converted from (R)-2-methyl-5-hexen-1-ol (as shown in Formula 23) through an esterification reaction, so this also shows that the optical purity of (R)-2-methyl-5-hexen-1-ol is greater than 99%; since (R)-2-methyl-5-hexen-1-ol is converted from (R)-4-isopropyl-3-((R)-2-methyl-5-hexenoyl)oxazolidin-2-one through a reduction reaction, this also shows that the optical purity of (R)-4-isopropyl-3-((R)-2-methyl-5-hexenoyl)oxazolidin-2-one (as shown in Formula 7) is greater than 99%.

[0047] Embodiment three: A method for synthesizing 1-(((5R,11S)-5,11-dimethylheptadecen-1-yl)-6-sulfonyl)-4-methylbenzene (as shown in Formula 15), wherein the synthetic route is shown in the following reaction formula: The synthesis method of 1-(((5R,11S)-5,11-dimethylheptadecen-1-yl)-6-sulfonyl)-4-methylbenzene (as shown in Formula 15) specifically comprises the following steps: A. Under argon protection, 9-boranebicyclo[3.3.1]nonene (9-BBN, 22.8 mL, 0.5 M in THF, 11.4 mmol) was slowly added to a dry tetrahydrofuran solution of (S)-5-methylundecene (as shown in Formula 10), wherein the 9-boranebicyclo[3.3.1]nonene was an existing chemical reagent, and the dry tetrahydrofuran solution of (S)-5-methylundecene (as shown in Formula 10) was obtained by uniformly mixing (S)-5-methylundecene (0.64 g, 3.8 mmol) with 10 mL of dry tetrahydrofuran; then, the mixture was stirred at room temperature for 12 hours, then cooled to 0° C., then sodium hydroxide solution (7.6 mL, 3 M, 22.8 mmol) was added, and stirred for 30 minutes; and After that, the temperature was lowered to -20°C, and a hydrogen peroxide solution (7.6 mL, 30 wt%) was slowly added; then, after stirring at room temperature for 3 hours, the reaction was quenched with a saturated aqueous ammonium chloride solution (15 mL) to obtain a reaction mass, and the reaction mass was separated to obtain an aqueous phase, and the separation process was completed. The aqueous phase was extracted with ethyl acetate for 3 times to obtain three organic phase samples, and the amount of ethyl acetate used in each extraction process was 50 mL; after mixing the three organic phases, the mixed organic phase was washed with brine (50 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure; the residue after reduced pressure concentration was purified by silica gel column chromatography (ethyl acetate / petroleum ether=1:10) to obtain (S)-5-methylundecanol (as shown in Formula 11, 0.57 g, yield 80%), which was a colorless oil; The specific rotation, nuclear magnetic resonance hydrogen spectrum, carbon spectrum and high-resolution mass spectrometry of (S)-5-methylundecanol were measured, and the results were as follows: [α] D 25 = -1.41 (c 0.85, CHCl3); 1 H NMR (400MHz, Chloroform-d) δ3.64(t,J=6.6Hz,2H),1.62–1.48(m,2H),1.43–1.19(m,14H),1.16–1.04(m,2H),0.94–0.79(m,6H); 13 CNMR(101MHz, CDCl3)δ63.25,37.16,36.98,33.30,32.89,32.09,29.82,27.17,23.36,22.84,19.77,14.26; HRMS(ESI,m / z):calculated for[M+Na] + C 12 H 26 ONa 209.1876,found:209.1882.

[0048] B), under argon protection, (S)-5-methyl undecyl alcohol (as shown in formula 11, 0.37 g, 2.0 mmol), triphenylphosphine (0.63 g, 2.4 mmol) and imidazole (0.30 g, 4.4 mmol) were placed in 5 mL of dry tetrahydrofuran and stirred evenly, and iodine dry tetrahydrofuran solution was slowly added, wherein the iodine dry tetrahydrofuran solution was obtained by mixing iodine element (0.61 g, 2.4 mmol) and 5 ml of dry tetrahydrofuran; then, the mixture was stirred at 25° C. for 3 hours, and then, 5 wt% Na2S2O 3 aqueous solution to quench the reaction to obtain a reaction mass, the reaction mass was separated to obtain an aqueous phase, the liquid separation process was completed, the aqueous phase was extracted with ethyl acetate 3 times to obtain three organic phase samples, and the amount of ethyl acetate used in each extraction process was 30 mL; the organic phase samples were mixed, and the mixed organic phase was washed with a Na2S2O3 aqueous solution (5wt%), water and brine, and dried over anhydrous sodium sulfate, and concentrated under reduced pressure; the residue after reduced pressure concentration was purified by silica gel column chromatography (petroleum ether) to obtain (S)-1-iodo-5-methylundecane (as shown in Formula 12, 0.52 g, 88% yield), which was a light yellow oil; The specific rotation, nuclear magnetic resonance hydrogen spectrum, carbon spectrum and high-resolution mass spectrometry of (S)-1-iodo-5-methylundecane were measured, and the results were as follows: [α] D 25 = +0.88 (c 0.90, CHCl3); 1 H NMR(500MHz,Chloroform-d)δ3.19(t,J=7.0Hz,2H),1.85–1.76(m,2H),1.45–1.34(m,3 H),1.32–1.24(m,10H),1.15–1.07(m,2H),0.88(t,J=6.9Hz,3H),0.85(d,J=6.6Hz,3H); 13 C NMR(126MHz, CDCl3)δ37.11,36.01,34.02,32.74,32.09,29.81,28.16,27.15,22.84,19.77,14.27,7.52; HRMS(ESI,m / z):calculated for[M+H] + C 12 H 26 I 297.1074, found:297.1063.

[0049] Under argon protection, (R)-2-methyl-5-hexen-1-ol (as shown in Formula 8, 0.29 g, 2.5 mmol), triphenylphosphine (0.79 g, 3.0 mmol) and imidazole (0.37 g, 5.5 mmol) were placed in 8 mL of dry tetrahydrofuran and stirred evenly, and a dry tetrahydrofuran solution of iodine was slowly added, wherein the dry tetrahydrofuran solution of iodine was obtained by mixing iodine (0.76 g, 3.0 mmol) and 8 ml of dry tetrahydrofuran evenly; after stirring for 3 hours, the reaction was quenched with a 5 wt % Na2S2O3 aqueous solution, A reaction material is obtained, and an aqueous phase is obtained after the reaction material is layered, and a liquid separation process is completed. The aqueous phase is extracted with ethyl acetate three times to obtain three organic phase samples, and the amount of ethyl acetate used in each extraction process is 40 mL; the three organic phases are mixed, and the mixed organic phase is washed with a Na2S2O3 aqueous solution (5wt%), water and brine, and dried over anhydrous sodium sulfate, and concentrated under reduced pressure; the residue after reduced pressure concentration is purified by silica gel column chromatography (petroleum ether) to obtain (R)-6-iodo-5-methyl-1-hexene (as shown in Formula 13, 0.45 g, yield 80%), which is a light yellow oil; The specific rotation, nuclear magnetic resonance hydrogen spectrum, carbon spectrum and high-resolution mass spectrometry of (R)-6-iodo-5-methyl-1-hexene were measured, and the results were as follows: [α] D 25 = -2.90 (c 0.83, CHCl3); 1 H NMR(500MHz,Chloroform-d)δ5.83–5.75(m,1H),5.05–5.01(m,1H),4.99–4.95(m,1H),3.24(dd,J=9.6,4.4Hz,1 H),3.17(dd,J=9.7,5.7Hz,1H),2.09–2.04(m,2H),1.52–1.45(m,2H),1.35–1.27(m,1H),0.99(d,J=6.4Hz,3H); 13 C NMR(126MHz, CDCl3)δ138.40,114.97,35.70,34.17,31.24,20.60,17.75; HRMS(ESI,m / z):calculated for[M+H] + C 17 H 14 I 225.0135, found:225.0145.

[0050] Under argon protection, sodium p-toluenesulfinate (0.25 g, 1.4 mmol), polyethylene glycol-400 (PEG-400, 3 mL) and dimethyl sulfoxide DMSO (1.5 mL) were mixed and stirred evenly, and then (R)-6-iodo-5-methyl-1-hexene (as shown in Formula 13, 0.22 g, 1.0 mmol) was slowly added; then heated to 80° C. and stirred for 2 hours; then cooled to room temperature, and the reaction was quenched with a 10 wt % sodium chloride solution (10 mL) to obtain a reaction mass, and the reaction mass was separated to obtain water phase, completing the liquid separation process, the aqueous phase was extracted with ethyl acetate three times to obtain three organic phase samples, the amount of ethyl acetate used in each extraction process was 40 mL, the three organic phase samples were mixed, the mixed organic phase was washed with water and brine, and dried over anhydrous sodium sulfate, and then concentrated in vacuo; the residue after vacuum concentration was purified by silica gel column chromatography (ethyl acetate / petroleum ether=1:8) to obtain (R)-1-methyl-4-((2-methyl-5-hexenyl)sulfonyl)benzene (as shown in Formula 14, 0.18 g, yield 70%), which was a colorless oil; The specific rotation, H NMR, C NMR and high resolution mass spectrometry of (R)-1-methyl-4-((2-methyl-5-hexenyl)sulfonyl)benzene were measured, and the results were as follows: [α] D 25 = -3.06 (c 0.95, CHCl3); 1 H NMR(500MHz,Chloroform-d)δ7.78(d,J=8.2Hz,2H),7.35(d,J=8.0Hz,2H),5.75–5.66(m,1H),4.99–4.89(m,2H),3.07(dd,J=14.2,4.7Hz,1H) ,2.91(dd,J=14.2,7.7Hz,1H),2.45(s,3H),2.15–2.05(m,1H),2.04–1. 92(m,2H),1.56–1.49(m,1H),1.37–1.29(m,1H),1.07(d,J=6.7Hz,3H); 13 C NMR(126MHz, CDCl3)δ144.63,137.95,137.36,130.02,128.04,115.15,62.75,35.93,30.76,28.29,21.76,19.87; HRMS(ESI,m / z):calculated for[M+H] + C 14 H 21 O2S253.1257, found:253.1259.

[0051] Under argon protection and -78°C, (R)-1-methyl-4-((2-methyl-5-hexenyl)sulfonyl)benzene (as shown in Formula 14, 0.15 g, 0.6 mmol) was dissolved in 10 mL of dry tetrahydrofuran, and n-butyl lithium n-BuLi (2.4 M, 0.38 mL, 0.9 mmol) was slowly added; then, stirred at -78°C for 30 minutes, then heated to -35°C and stirred for 30 minutes; then cooled to -78°C, and a mixed solution of hexamethylphosphoramide HMPA (0.42 mL), dry tetrahydrofuran (1 mL) and (S)-1-iodo-5-methylundecane (as shown in Formula 12, 0.21 g, 0.72 mmol) was slowly added; then, heated to -35°C and stirred for 30 minutes. Warm to room temperature and stir overnight; then, add 1M hydrochloric acid (6mL) to quench, and obtain a reaction mass. After the reaction mass is separated, an aqueous phase is obtained, and the separation process is completed. The aqueous phase is extracted with ethyl acetate for 3 times to obtain three organic phase samples, and the amount of ethyl acetate used in each extraction process is 20mL; the three organic phase samples are mixed, and the mixed organic phase is washed with a saturated sodium bicarbonate solution and brine, and then dried over anhydrous sodium sulfate, and then concentrated in vacuo; the residue after vacuum concentration is purified by silica gel column chromatography (ethyl acetate / petroleum ether=1:10) to obtain 1-(((5R,11S)-5,11-dimethylheptadecen-1-yl)-6-sulfonyl)-4-methylbenzene (as shown in Formula 15, 0.19 g, yield 75%), which is a colorless oil; The specific rotation, H NMR, C NMR and high resolution mass spectrometry of 1-(((5R,11S)-5,11-dimethylheptadecen-1-yl)-6-sulfonyl)-4-methylbenzene were measured. The results are as follows: [α] D 25 =-0.38 (c 1.04, CHCl3); H NMR(500MHz,Chloroform-d)δ7.75(d,J=8.1Hz,2H),7.34(d,J=8.0Hz,2H),5 .80–5.62(m,1H),5.01–4.89(m,2H),2.91–2.85(m,1H),2.45(s,3H),2.23–2 .10(m,1H),2.04–1.81(m,3H),1.66–1.61(m,1H),1.40–1.35(m,1H),1.33–1 .11(m,17H),1.04–1.00(m,3H),0.88(t,J=6.9Hz,3H),0.79(d,J=6.5Hz,3H); 13C NMR(126MHz, CDCl3)δ144.39,137.91(138.50),136.54(136.86),129.86(129.83),128.7 3(128.70),115.18(114.97),68.30(69.70),37.16(37.13),36.69(36.72),35.18,32.73( 32.78),32.27,32.09(31.99),31.59,31.48(31.06),29.81,29.49(29.19),27.16(27.04 ),25.14,22.84(23.92),21.74,19.74(18.09),14.85,14.27; HRMS(ESI,m / z):calculated for[M+H] + C 26 H 45 O2S 421.3135,found:421.3117.

[0052] Embodiment 4: A method for synthesizing (5R, 11S)-5,11-dimethylheptadecane (i.e., component 1 of the sex pheromone of western hemlock looper, whose structural formula is shown in Formula 1), and its synthetic route is shown in the following reaction formula: The synthesis method of the western hemlock looper sex pheromone (5R, 11S)-5,11-dimethylheptadecane specifically comprises the following steps: (1) Under argon protection, magnesium powder (0.13 g, 5.4 mmol) was dissolved in dry tetrahydrofuran (1.0 mL), and MeMgBr (3.0 M, two drops) was added; after stirring at room temperature for 15 minutes, a dry methanol solution of 1-(((5R,11S)-5,11-dimethylheptadecene-1-yl)-6-sulfonyl)-4-methylbenzene (as shown in Formula 15) was slowly added, wherein the dry methanol solution of 1-(((5R,11S)-5,11-dimethylheptadecene-1-yl)-6-sulfonyl)-4-methylbenzene is 1-(((5R,11S)-5,11-dimethylheptadecene-1-yl)-6-sulfonyl)-4-methylbenzene -4-methylbenzene (0.15 g, 0.35 mmol) and 5.0 mL of dry methanol were uniformly mixed; then stirred at 50°C for 4 hours; then, concentrated to remove methanol, and then added cold 1M hydrochloric acid solution (2 mL) to quench the reaction to obtain a reaction mass. After the reaction mass was layered, an aqueous phase was obtained. After the separation process was completed, the aqueous phase was extracted with ether for 3 times to obtain three organic phase samples. The amount of ether used in each extraction process was 10 mL. The three organic phase samples were mixed, and the mixed organic phase was washed with a saturated sodium bicarbonate solution and brine, and dried over anhydrous sodium sulfate, and concentrated in vacuo to obtain a crude product of (5S, 11S)-5,11-dimethylheptadecan-1-ene; Under the protection of hydrogen, the crude product (5S,11S)-5,11-dimethylheptadecan-1-ene was dissolved in 3 mL of methanol to obtain a methanol solution of the crude product (5S,11S)-5,11-dimethylheptadecan-1-ene, which was then added to a methanol suspension containing palladium carbon, wherein the methanol suspension containing palladium carbon was obtained by uniformly mixing palladium carbon (30 mg) and methanol (2 ml); then, the mixture was stirred at 25° C. for 12 hours, and then vacuum concentrated; the residue after vacuum concentration was purified by silica gel column chromatography (petroleum ether) to obtain (5R,11S)-5,11-dimethylheptadecane (63.9 mg, yield 68%), which was a colorless oil; (5R,11S)-5,11-dimethylheptadecane was measured by specific rotation, nuclear magnetic resonance hydrogen spectrum, carbon spectrum and high-resolution mass spectrometry, and the results were as follows: [α] D 25 = -0.93 (c 0.63, CHCl3); 1 H NMR(500MHz,Chloroform-d)δ1.41–1.33(m,2H),1.31–1.21(m,22H),1.14–1.03(m,4H),0.91–0.87(m,6H),0.86–0.81(m,6H); 13CNMR (126MHz, CDCl3) δ37.27,36.94,32.92,32.90,32.13,30.54,30.20,29.90,29.86 ,29.51,27.28,27.21,23.21,22.86,19.89,14.33,14.28; HRMS(ESI,m / z):calculated for[M+K] + C 19 H 40 K307.2762, found:307.2751.

[0053] Embodiment five: A method for synthesizing (S)-7-methylheptadecane (i.e., component 2 of the sex pheromone of western hemlock looper, whose structural formula is shown in Formula 2), and whose synthetic route is shown in the following reaction formula: The synthesis method of the western hemlock looper sex pheromone (S)-7-methylheptadecane comprises the following steps: Under argon protection, a dichloromethane solution of p-toluenesulfonyl chloride was slowly added to a dichloromethane solution containing (S)-5-methylheptadecanol (as shown in Formula 11) and triethylamine, wherein the dichloromethane solution of p-toluenesulfonyl chloride was obtained by uniformly mixing p-toluenesulfonyl chloride (0.19 g, 1.0 mmol) and dichloromethane (2 mL), and the dichloromethane solution containing (S)-5-methylheptadecanol (as shown in Formula 11) and triethylamine was obtained by uniformly mixing (S)-5-methylheptadecanol (0.57 g, 0.5 mmol) and triethylamine (0.12 mL, 0.88 mmol) and a dichloromethane solution (2 mL). ml) were mixed evenly; then, stirred at room temperature for 18 hours; then, the reaction was quenched with a saturated sodium bicarbonate solution (4 mL) to obtain a reaction mass, and the reaction mass was separated to obtain an aqueous phase, and the separation process was completed. The aqueous phase was extracted with dichloromethane 3 times to obtain three organic phase samples, and the amount of dichloromethane used in each extraction process was 15 mL; the three organic phase samples were mixed, and the mixed organic phase was washed with brine (20 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure; the residue after reduced pressure concentration was purified by silica gel column chromatography (ethyl acetate / petroleum ether=1:5) to obtain a p-toluenesulfonate product in the form of a colorless oil; Under argon protection and -20 ° C, Li2CuCl4 (0.5 mL, 0.05 mmol) and hexylmagnesium bromide (as shown in Formula 16, 1.5 mL, 1.5 mmol) were added to a dry tetrahydrofuran solution of p-toluenesulfonate, wherein hexylmagnesium bromide in the present application is an existing reagent, and the dry tetrahydrofuran solution of p-toluenesulfonate is obtained by uniformly mixing p-toluenesulfonate (0.5 mmol, 1.0 equivalent) and dry tetrahydrofuran (2 mL); then, the temperature was raised to room temperature and stirred overnight, and then saturated The reaction was quenched with ammonium chloride solution (5 mL) to obtain a reaction mass, and the reaction mass was separated to obtain an aqueous phase, and the separation process was completed. The aqueous phase was extracted with ethyl acetate three times to obtain three organic phase samples, and the amount of ethyl acetate used in each extraction process was 30 mL; the three organic phase samples were mixed, and the mixed organic phase was washed with brine (30 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure; the residue after reduced pressure concentration was purified by silica gel column chromatography (petroleum ether) to obtain (S)-7-methylheptadecane (98 mg, yield 77%), which was a colorless oil; The specific rotation, nuclear magnetic resonance hydrogen spectrum, carbon spectrum and high-resolution mass spectrometry of (S)-7-methylheptadecane were measured, and the results are as follows: [α] D 25 =-1.76(c 0.87, CHCl3); H NMR (400MHz, Chloroform-d) δ1.38–1.03(m,28H),1.09–1.04(m,1H),0.90–0.82(m,9H); 13 C NMR(101MHz, CDCl3)δ37.27,32.92,32.13,32.10,30.21,29.90,29.87,29.83,29.53,27.25,27.22,22.86,19.88,14.28; HRMS(ESI,m / z):calculated for[M+K] + C 18 H 38 K 293.2605, found:293.2601.

[0054] Embodiment six: The synthesis method of (S)-2,5-dimethylheptadecane (i.e., component 3 of the sex pheromone of western hemlock looper, whose structural formula is shown in Formula 3) is shown in the following reaction formula: The synthesis method of (S)-2,5-dimethylheptadecane specifically comprises the following steps: Under argon protection, tetradecanoic acid (as shown in Formula 17, 0.91 g, 4 mmol) was dissolved in dry dichloromethane (DCM, 6 ml), and the temperature was adjusted to 0°C; then, oxalyl chloride (0.76 g, 6 mmol) and 0.1 ml of methylformamide (DMF) were slowly added, and then stirred at 0°C for 2 hours; then, the solvent was removed under reduced pressure to obtain a slightly yellow crude product of acyl chloride; Under argon protection and 0°C, sodium hydride (NaH 60% mineral oil, 0.15 g, 3.3 mmol) was dissolved in dry tetrahydrofuran (6 ml); then, a dry tetrahydrofuran solution of (S)-4-isopropyloxazolidin-2-one (as shown in Formula 5) was slowly added, the temperature was raised to 25°C and stirred for 2 hours; then the temperature was lowered to 0°C, and then a dry tetrahydrofuran solution of the crude product acid chloride was slowly added, and then stirred at room temperature for 4 hours, and the reaction was quenched with a saturated aqueous ammonium chloride solution (10 ml) to obtain a reaction mass, wherein the dry tetrahydrofuran solution of (S)-4-isopropyloxazolidin-2-one was obtained by uniformly mixing (S)-4-isopropyloxazolidin-2-one (0.67 g, 5.2 mmol) and dry tetrahydrofuran (6 ml). ; The dry tetrahydrofuran solution of the crude acid chloride is obtained by uniformly mixing the slightly yellow crude acid chloride and 10 ml of dry tetrahydrofuran; the reaction materials are separated to obtain an aqueous phase, and the separation process is completed. The aqueous phase is extracted with ethyl acetate three times to obtain three organic phase samples, and the amount of ethyl acetate used in each extraction process is 30 ml; the three organic phase samples are mixed, and the mixed organic phase is washed with brine (30 ml), dried over anhydrous sodium sulfate, and concentrated under reduced pressure; the residue after reduced pressure concentration is purified by silica gel column chromatography (ethyl acetate / petroleum ether=1:5) to obtain (S)-4-isopropyl-3-tetradecanoyl oxazolidin-2-one (as shown in Formula 19), which is a light yellow oil (1.15 g, yield 85%); The specific rotation, H NMR, C NMR and high resolution mass spectrometry of (S)-4-isopropyl-3-tetradecanoyloxazolidin-2-one were measured, and the results were as follows: [α] D 25 = +56.03 (c 3.02, CHCl3); 1H NMR(500MHz,Chloroform-d)δ4.44–4.41(m,1H),4.25(t,J=8.7Hz,1H),4.19(dd,J=9.1,3.0Hz,1H),3.00–2.94(m,1H), 2.87–2.81(m,1H),2.41–2.32(m,1H),1.69–1.59(m,2H),1.35–1.24(m,20H),0.90(d,J=7.1Hz,3H),0.88–0.86(m,6H); 13 C NMR (126MHz, CDCl3) δ173.56,154.20,63.42,58.50,35.65,32.04,29.80,29.77,29.73,29.61 ,29.50,29.48,29.26,28.51,24.60,22.81,18.10,14.78,14.24; HRMS(ESI,m / z):calculated for[M+K] + C 20 H 37 O3NK 378.2405,found:378.2405.

[0055] Under argon protection and -78°C, (S)-4-isopropyl-3-tetradecanoyl oxazolidin-2-one (as shown in Formula 19, 1.02 g, 3 mmol) was dissolved in dry tetrahydrofuran (8 ml); then, sodium hexamethyldisilazide (2.25 ml, 4.5 mmol) was slowly added, and after stirring for 1 hour, iodomethane (0.93 ml, 15 mmol) was added dropwise, wherein sodium hexamethyldisilazide was an existing reagent with a specification of (2.0 M, in THF); then, the mixture was stirred at -78°C for 2 hours, and then the temperature was raised to -60°C and stirred for 3 hours; then, a saturated aqueous ammonium chloride solution (1 0ml) to quench the reaction to obtain a reaction mass; after the reaction mass was separated, an aqueous phase was obtained, and the separation process was completed. The aqueous phase was extracted with ethyl acetate for 3 times to obtain three organic phase samples, and the amount of ethyl acetate used in each extraction process was 30ml. The three organic phase samples were mixed, and the mixed organic phase was washed with brine (30ml), dried over anhydrous sodium sulfate, and concentrated under reduced pressure; the residue after reduced pressure concentration was purified by silica gel column chromatography (ethyl acetate / petroleum ether=1:8) to obtain (S)-4-isopropyl-3-((S)-2-methyltetradecanoyl)oxazolidin-2-one (20) as a colorless oil (0.83g, yield 78%); The specific rotation, H NMR, C NMR and high resolution mass spectrometry of (S)-4-isopropyl-3-((S)-2-methyltetradecanoyl)oxazolidin-2-one were measured, and the results were as follows: [α] D 25 = +60.61 (c 1.96CHCl3); 1 H NMR(500MHz,Chloroform-d)δ4.46–4.43(m,1H),4.25(t,J=8.7Hz,1H),4.20(dd,J=9.1,2.9Hz,1H),3.75–3.68(m,1H),2.38–2.32 (m,1H),1.74–1.66(m,1H),1.38–1.32(m,1H),1.30–1.23(m,20H),1.19(d,J=6.9Hz,3H),0.91(d,J=7.0Hz,3H),0.89–0.86(m,6H); 13 C NMR (126MHz, CDCl3) δ177.46,153.80,63.32,58.57,37.86,33.26,32.06,29.81,29.81,29.78,29 .73,29.65,29.50,28.57,27.45,22.82,18.08,17.99,14.82,14.25; HRMS(ESI,m / z):calculated for[M+Na] + C 21 H 39 O3NNa378.2822,found:378.2813; Under argon protection and 0°C, LiAlH4 (0.24 g, 6.3 mmol) was dissolved in dry tetrahydrofuran (3 ml), and then a dry tetrahydrofuran solution of (S)-4-isopropyl-3-((S)-2-methyltetradecanoyl)oxazolidin-2-one (as shown in Formula 20) was slowly added dropwise for 20 minutes. The dry tetrahydrofuran solution of (S)-4-isopropyl-3-((S)-2-methyltetradecanoyl)oxazolidin-2-one was prepared by dissolving (S)-4-isopropyl-3-((S)-2-methyltetradecanoyl)oxazolidin-2-one (0.64 g, 1.8 m mol) and dry tetrahydrofuran (5 ml) were uniformly mixed; then the temperature was raised to 25° C. and stirred for 12 hours, and then a saturated aqueous ammonium chloride solution (10 ml) was slowly added to quench the reaction to obtain a reaction mass, and then the reaction mass was diluted with ethyl acetate; the precipitate was filtered off, and the filtrate was dried over anhydrous sodium sulfate and then filtered to obtain a filtrate, and the filtrate was concentrated under reduced pressure; the residue after concentration under reduced pressure was purified by silica gel column chromatography (ethyl acetate / petroleum ether=1:5) to obtain (S)-2-methyltetradecanol (as shown in Formula 21) in the form of a colorless oil (0.35 g, yield 81%, ≥99% ee); The optical purity of (S)-2-methyltetradecanol was determined by NMR of Mosher ester derived from (S)-2-methyltetradecanol; (S)-2-methyltetradecanol was determined by specific rotation, H NMR, C NMR and high resolution mass spectrometry, and the results are as follows: [α] D 25 = -10.60 (c 1.10, CHCl3); 1 H NMR(500MHz,Chloroform-d)δ3.51(dd,J=10.5,5.8Hz,1H),3.42(dd,J=10.5,6.6Hz,1H),1.64–1.57(m,1H ),1.39–1.35(m,2H),1.31–1.26(s,20H),1.13–1.07(m,1H),0.91(d,J=6.7Hz,3H),0.88(t,J=7.0Hz,3H); 13 CNMR(126MHz, CDCl3)δ68.58,35.92,33.30,32.07,30.10,29.83,29.81,29.80,29.51,27.13,22.84,16.73,14.26; HRMS(ESI,m / z):calculated for[M+Na] + C 15 H 32 ONa 251.2345,found:251.2364.

[0056] Under argon protection, a dry dichloromethane solution containing (S)-2-methyltetradecanol (as shown in Formula 21) and triethylamine was slowly added to a dry dichloromethane solution of p-toluenesulfonyl chloride, wherein the dry dichloromethane solution of p-toluenesulfonyl chloride was obtained by uniformly mixing p-toluenesulfonyl chloride (0.30 g, 1.6 mmol) and dry dichloromethane (4 mL), and the dry dichloromethane solution containing (S)-2-methyltetradecanol (as shown in Formula 21) and triethylamine was obtained by uniformly mixing (S)-2-methyltetradecanol (0.18 g, 0.8 mmol) and triethylamine (0.2 mL, 1.4 mmol) and dry The mixture was uniformly mixed with dichloromethane (5 mL); then, stirred at room temperature for 18 hours; then, quenched with a saturated sodium bicarbonate aqueous solution (5 mL) to obtain a reaction mass, and the reaction mass was layered to obtain an aqueous phase, and the liquid separation process was completed. The aqueous phase was extracted with dichloromethane for 3 times to obtain three organic phase samples, and the amount of dichloromethane used in each extraction process was 20 mL; the three organic phase samples were mixed, and the mixed organic phase was washed with brine (20 mL), dried over anhydrous sodium sulfate, and then concentrated under reduced pressure; the residue after concentrated under reduced pressure was purified by silica gel column chromatography (ethyl acetate / petroleum ether=1:5) to obtain p-toluenesulfonic acid The crude product of p-toluenesulfonate is in the form of a colorless oil. Under argon protection and at -20°C, Li2CuCl4 (0.8 ml, 0.08 mmol) is added to a dry tetrahydrofuran solution of the crude product of p-toluenesulfonate, wherein the dry tetrahydrofuran solution of the crude product of p-toluenesulfonate is obtained by uniformly mixing the crude product of p-toluenesulfonate (0.8 mmol, 1.0 equivalent) and dry tetrahydrofuran (2 mL), and Li2CuCl4 is a commercial reagent. Then, isobutylmagnesium bromide (as shown in Formula 22, 4.8 mL, 2.4 mmol) is slowly added. Isobutylmagnesium bromide is an existing reagent with a specification of 0.5 M , and then warmed to room temperature and stirred overnight; then quenched the reaction with a saturated aqueous solution of ammonium chloride (5 mL) to obtain a reaction mass, and after the reaction mass was layered, an aqueous phase was obtained, and the separation process was completed. The aqueous phase was extracted with ethyl acetate three times to obtain three organic phase samples, and the amount of ethyl acetate used in each extraction process was 20 mL; the three organic phase samples were mixed, and the mixed organic phase was washed with brine (20 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure; the residue after reduced pressure concentration was purified by silica gel column chromatography (petroleum ether) to obtain (S)-2,5-dimethylheptadecane (as shown in Formula 3, 0.15 g, yield 72%), which was a colorless oil; The specific rotation, nuclear magnetic resonance hydrogen spectrum, carbon spectrum and high-resolution mass spectrometry of (S)-2,5-dimethylheptadecane were measured, and the results are as follows: [α] D 25 = -0.77 (c 1.04, CHCl3); 1H NMR(400MHz,Chloroform-d)δ1.51–1.43(m,1H),1.34–1.23(m,23H),1.18–1.05(m,4H),0.90–0.83(m,12H); 13 C NMR (101MHz, CDCl3) δ37.27,36.55,34.93,33.18,32.10,30.21,29.90,29.87,29.83, 29.53,28.50,27.26,22.99,22.86,22.76,19.92,14.28; HRMS(ESI,m / z):calculated for[M+K] + C 19 H 32 NO3307.2762, found:307.2758.

[0057] Embodiment seven: A method for synthesizing (5R, 11S)-5,11-dimethylheptadecane (i.e., component 1 of the sex pheromone of western hemlock looper, the structural formula of which is shown in formula 1), comprising the following steps: First, (R)-4-isopropyl-3-((R)-2-methyl-5-hexenoyl)oxazolidine-2-one (as shown in Formula 7) is used as a raw material to synthesize (S)-5-methylundecene (as shown in Formula 10); wherein the synthesis method of the (R)-4-isopropyl-3-((R)-2-methyl-5-hexenoyl)oxazolidine-2-one (as shown in Formula 7) is consistent with the synthesis method of the (R)-4-isopropyl-3-((R)-2-methyl-5-hexenoyl)oxazolidine-2-one described in Example 1; the preparation method of the (S)-5-methylundecene is consistent with the synthesis method of the (S)-5-methylundecene described in Example 2; Then, (S)-5-methylundecene (as shown in Formula 10) is used as a raw material to synthesize 1-(((5R,11S)-5,11-dimethylheptadecene-1-yl)-6-sulfonyl)-4-methylbenzene (as shown in Formula 15); wherein the synthesis method of the 1-(((5R,11S)-5,11-dimethylheptadecene-1-yl)-6-sulfonyl)-4-methylbenzene is consistent with the synthesis method of the 1-(((5R,11S)-5,11-dimethylheptadecene-1-yl)-6-sulfonyl)-4-methylbenzene described in Example 3; Finally, 1-(((5R,11S)-5,11-dimethylheptadecane-1-yl)-6-sulfonyl)-4-methylbenzene (as shown in Formula 15) was used as a raw material to synthesize (5R,11S)-5,11-dimethylheptadecane (i.e., component 1 of the western hemlock looper sex pheromone), as shown in Formula 1); wherein the synthesis method of the (5R,11S)-5,11-dimethylheptadecane is consistent with the synthesis method of the (5R,11S)-5,11-dimethylheptadecane described in Example 4.

[0058] Embodiment eight: A method for synthesizing (S)-7-methylheptadecane (i.e., component 2 of the sex pheromone of western hemlock looper, the structural formula of which is shown in Formula 2), comprising the following steps: First, (R)-4-isopropyl-3-((R)-2-methyl-5-hexenoyl)oxazolidine-2-one (as shown in Formula 7) is used as a raw material to synthesize (S)-5-methylundecene (as shown in Formula 10); wherein the synthesis method of the (R)-4-isopropyl-3-((R)-2-methyl-5-hexenoyl)oxazolidine-2-one (as shown in Formula 7) is consistent with the synthesis method of the (R)-4-isopropyl-3-((R)-2-methyl-5-hexenoyl)oxazolidine-2-one described in Example 1; the preparation method of the (S)-5-methylundecene is consistent with the synthesis method of the (S)-5-methylundecene described in Example 2; Then, (S)-5-methylundecene (as shown in Formula 10) is used as a raw material to synthesize (S)-5-methylundecyl alcohol (as shown in Formula 11); wherein the synthesis method of the (S)-5-methylundecyl alcohol is consistent with the method for synthesizing (S)-5-methylundecyl alcohol in Step A of Example 3; Finally, (S)-5-methylundecanol (as shown in Formula 11) is used as a raw material to synthesize (S)-7-methylheptadecane (i.e., component 2 of the western hemlock looper sex pheromone), as shown in Formula 2); wherein the synthesis method of the (S)-7-methylheptadecane is consistent with the synthesis method of the (S)-7-methylheptadecane described in Example 5.

Claims

1. A R )-4-isopropyl-3-(( R )-2-methyl-5-hexenoyl)oxazolidin-2-one, characterized in that: Its structural formula is shown in Formula 7: 。 2. A R )-4-isopropyl-3-(( R )-2-methyl-5-hexenoyl)oxazolidine-2-one synthesis method, characterized in that: Said R )-4-isopropyl-3-(( R )-2-methyl-5-hexenoyl)oxazolidin-2-one is the ( R )-4-isopropyl-3-(( R )-2-methyl-5-hexenoyl)oxazolidin-2-one, the ( R )-4-isopropyl-3-(( R )-2-methyl-5-hexenoyl)oxazolidine-2-one synthesis method, comprising the following steps: S1, using 5-hexenoic acid as the starting material, and ( R )-4-isopropyloxazolidin-2-one reaction synthesis ( R )-3-(5-hexenoyl)-4-isopropyloxazolidin-2-one; S2, synthesis by chiral induced asymmetric methylation reaction ( R )-4-isopropyl-3-(( R )-2-methyl-5-hexenoyl)oxazolidin-2-one.

3. A S )-5-methylundecene, characterized in that: Said S )-5-Methylundecene is a R )-4-isopropyl-3-(( R )-2-methyl-5-hexenoyl)oxazolidin-2-one as a raw material, the ( R )-4-isopropyl-3-(( R )-2-methyl-5-hexenoyl)oxazolidin-2-one is the ( R )-4-isopropyl-3-(( R )-2-methyl-5-hexenoyl)oxazolidin-2-one.

4. A S )-5-methylundecene synthesis method, characterized in that: Said S )-5-methylundecene is the ( S )-5-methylundecene; said ( S )-5-methylundecene synthesis method, comprising the following steps: ,Will( R )-4-isopropyl-3-(( R )-2-methyl-5-hexenoyl)oxazolidin-2-one was reduced by LiAlH4 to obtain ( R )-2-methyl-5-hexen-1-ol; said ( R )-4-isopropyl-3-(( R )-2-methyl-5-hexenoyl)oxazolidin-2-one is the ( R )-4-isopropyl-3-(( R )-2-methyl-5-hexenoyl)oxazolidin-2-one; 2) Then ( R )-2-methyl-5-hexen-1-ol was activated by reaction with TsCl, and then coupled with amylmagnesium bromide under the catalysis of Li2CuCl4 to prepare ( S )-5-methylundecene.

5. A 1-((( 5R,11S )-5,11-dimethylheptadecen-1-yl)-6-sulfonyl)-4-methylbenzene, characterized in that: The 1-((( 5R,11S )-5,11-dimethylheptadecen-1-yl)-6-sulfonyl)-4-methylbenzene is used ( S )-5-methylundecene as a raw material, the ( S )-5-methylundecene is the ( S )-5-methylundecene.

6. A 1-(((5 R ,11 S A method for synthesizing 5,11-dimethylheptadecen-1-yl)-6-sulfonyl)-4-methylbenzene, characterized in that: 1-(((5 R ,11 S )-5,11-dimethylheptadecen-1-yl)-6-sulfonyl)-4-methylbenzene is the 1-(((5 R ,11 S )-5,11-dimethylheptadecen-1-yl)-6-sulfonyl)-4-methylbenzene; the 1-(((5 R ,11 S The method for synthesizing 4-methylbenzene comprises the following steps: A. S )-5-methylundecene is subjected to hydroboration and oxidation to synthesize (S)-5-methylundecyl alcohol, and then ( S )-5-methylundecyl alcohol was iodinated to synthesize the chiral intermediate ( S )-1-iodo-5-methylundecane; said ( S )-5-methylundecene is the ( S )-5-methylundecene; B. Use ( R )-2-methyl-5-hexen-1-ol was subjected to iodination reaction to synthesize ( R )-6-iodo-5-methyl-1-hexene, then ( R )-6-iodo-5-methyl-1-hexene p -Me(C6H4)SO2Na to react and synthesize ( R )-1-methyl-4-((2-methyl-5-hexenyl)sulfonyl)benzene, and then, R )-1-methyl-4-((2-methyl-5-hexenyl)sulfonyl)benzene and chiral intermediate ( S )-1-iodo-5-methylundecane undergoes alkylation reaction to synthesize 1-(((5 R ,11 S )-5,11-dimethylheptadecen-1-yl)-6-sulfonyl)-4-methylbenzene.

7. A (5 R ,11 S )-5,11-dimethylheptadecane, characterized in that: The (5 R ,11 S The structural formula of )-5,11-dimethylheptadecane is shown in Formula 1: ； The (5 R ,11 S )-5,11-dimethylheptadecane is produced by using 1-(((5 R ,11 S )-5,11-dimethylheptadecen-1-yl)-6-sulfonyl)-4-methylbenzene; the 1-(((5 R ,11 S )-5,11-dimethylheptadecen-1-yl)-6-sulfonyl)-4-methylbenzene is the 1-(((5 R ,11 S )-5,11-dimethylheptadecen-1-yl)-6-sulfonyl)-4-methylbenzene.

8. A ( S )-7-methylheptadecane, characterized in that: The S )-7-methylheptadecane has a structural formula as shown in Formula 2: ； Said S )-7-Methylheptadecane is made from ( S )-5-methyl undecyl alcohol as raw material; the ( S )-5-methylundecyl alcohol is the ( S )-5-methylundecanol.

9. A (5 R ,11 S )-5,11-dimethylheptadecane synthesis method, characterized by: Includes the following step: First, with ( R )-4-isopropyl-3-(( R )-2-methyl-5-hexenoyl)oxazolidin-2-one as raw material, synthesize ( S )-5-methylundecene; said ( R )-4-isopropyl-3-(( R )-2-methyl-5-hexenoyl)oxazolidin-2-one is the ( R )-4-isopropyl-3-(( R )-2-methyl-5-hexenoyl)oxazolidin-2-one; Then, with ( S )-5-methylundecene as raw material to synthesize 1-(((5 R ,11 S )-5,11-dimethylheptadecen-1-yl)-6-sulfonyl)-4-methylbenzene; Finally, 1-(((5 R ,11 S )-5,11-dimethylheptadecen-1-yl)-6-sulfonyl)-4-methylbenzene as raw material to synthesize (5 R ,11 S )-5,11-dimethylheptadecane.

10. A ( S )-7-methylheptadecane synthesis method, characterized in that: Includes the following step: First, with ( R )-4-isopropyl-3-(( R )-2-methyl-5-hexenoyl)oxazolidin-2-one as raw material, synthesize ( S )-5-methylundecene; said ( R )-4-isopropyl-3-(( R )-2-methyl-5-hexenoyl)oxazolidin-2-one is the ( R )-4-isopropyl-3-(( R )-2-methyl-5-hexenoyl)oxazolidin-2-one; Then, with ( S )-5-methylundecene as raw material, synthesize ( S )-5-methylundecanol; Finally, with ( S )-5-methyl undecyl alcohol as raw material, synthesize ( S )-7-methylheptadecane.

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