8-tert-butyldiphenylsilyloxy-7-methyl octyl p-toluenesulfonate as well as synthesis method and application thereof

Abstract

The invention discloses p-toluenesulfonic acid 8-tert-butyl diphenyl silyloxy-7-methyl octyl ester as well as a synthesis method and application thereof, and relates to the technical field of biopesticides. The preparation method comprises the following steps: taking 8-bromocaprylic acid as an initial raw material, and firstly reacting with t-BuOK and 18-crown ether-6; then reacting with pivaloyl chloride to generate acid anhydride, and then carrying out acylation reaction with 4-benzyl oxazolidine-2-ketone; then carrying out diastereoselective methylation; then, NaBH4 reduction is carried out; carrying out hydroxyl protection; then carrying out hydroboration oxidation reaction; and then carrying out TsCl sulfonylation, so as to synthesize the p-toluenesulfonic acid-8-tert-butyl diphenyl silyloxy 7-methyl octyl ester. The optical purity of the (S)-p-toluenesulfonic acid 8-tert-butyl diphenyl silyloxy-7-methyl octyl ester synthesized in the invention reaches 98%, and the optical purity of the (R)-p-toluenesulfonic acid 8-tert-butyl diphenyl silyloxy-7-methyl octyl ester synthesized in the invention also reaches 98%.

Description

Technical Field

[0001] This invention belongs to the field of biological pesticide technology, specifically relating to a p-toluenesulfonic acid 8-tert-butyldiphenylsilyloxy-7-methyloctyl ester, its synthesis method, and its application. Background Technology

[0002] The German cockroach (Blattella germanica) is a widespread and difficult-to-control sanitary pest, not only a significant vector for various diseases but also a major indoor allergen. Currently, highly effective poison baits are the primary method for controlling German cockroaches. However, long-term use of single insecticides can lead to strong resistance, and passive contact with chemical pesticides is not always effective. Therefore, researchers have begun to consider using aggregation pheromones as attractants in combination with insecticides to control German cockroaches. This approach not only reduces the amount of insecticide used but also significantly increases the effectiveness of attracting and killing them. The aggregation pheromone of the German cockroach is complex. In 2002, Rivault and his team analyzed the surface extract of the German cockroach in their paper "Are Differences in Hydrocarbon Profiles Able to Mediate Strain Recognition in German Cockroaches (Dictyoptera: Blattellidae)? European Journal of Entomology, 2002, 99(4): 437-444." and found that 3,11-dimethylnonacontane was the most abundant substance in the aggregation pheromone of the German cockroach. Currently, there are no literature reports on the synthesis of 8-tert-butyldiphenylsilyloxy-7-methyloctyl p-toluenesulfonic acid, an important intermediate for the synthesis of 3,11-dimethylnonacontane. Furthermore, conducting research on the asymmetric synthesis of 8-tert-butyldiphenylsilyloxy-7-methyloctyl p-toluenesulfonic acid not only overcomes the yield bottleneck of natural extraction and provides compounds for further research on its biological activity, but also provides theoretical support for the molecular design of novel aggregation behavior disruptors, further promoting the development of environmentally compatible German small sickle control technology. Therefore, this application provides 8-tert-butyldiphenylsilyloxy-7-methyloctyl p-toluenesulfonic acid, its synthesis method, and its applications. Summary of the Invention

[0003] To overcome the shortcomings of the prior art, the present invention provides 8-tert-butyldiphenylsilyloxy-7-methyloctyl p-toluenesulfonic acid, its synthesis method and application.

[0004] The technical solution of this invention is as follows: A p-toluenesulfonic acid 8-tert-butyldiphenylsilyloxy-7-methyloctyl ester, the structural formula of which is shown below: .

[0005] Preferably, the p-toluenesulfonic acid 8-tert-butyldiphenylsilyloxy-7-methyloctyl ester is in the S configuration, and the structural formula of the S-configured p-toluenesulfonic acid 8-tert-butyldiphenylsilyloxy-7-methyloctyl ester is shown in formula (S)-10: .

[0006] Preferably, the 8-tert-butyldiphenylsilyloxy-7-methyloctyl p-toluenesulfonic acid ester has the R configuration, and the structural formula of the R-configured 8-tert-butyldiphenylsilyloxy-7-methyloctyl p-toluenesulfonic acid ester is shown in formula (R)-10: .

[0007] A method for synthesizing p-toluenesulfonic acid-8-tert-butyldiphenylsilyloxy-7-methyloctyl ester includes the following steps: starting with 8-bromooctanoic acid, it is first reacted with t-BuOK and 18-crown ether-6; then reacted with pentanoyl chloride to generate an anhydride, followed by acylation with 4-benzyloxazolidine-2-one; then diastereoselective methylation; then reduction with NaBH4; then hydroxyl protection using TBDPSCl; then hydroboration oxidation to oxidize the olefin to an alcohol; and finally sulfonation with TsCl to synthesize p-toluenesulfonic acid-8-tert-butyldiphenylsilyloxy-7-methyloctyl ester.

[0008] Preferably, the method for synthesizing p-toluenesulfonic acid-8-tert-butyldiphenylsilyloxy-7-methyloctyl ester includes the following steps: S1. Oct-7-enoic acid was synthesized by reacting 8-bromooctanoic acid with t-BuOK and 18-crown ether-6 as the starting material. S2, octyl-7-enoic acid reacts with pivaloyl chloride to form an acid anhydride, which is then acylated with 4-benzyloxazolidine-2-one to synthesize 4-benzyl-3-octyl-7-enoyloxazolidine-2-one; S3. 4-Benzyl-3-(2-methyloctyl-7-enoyl)oxazolidin-2-one was synthesized by diastereoselective methylation of 4-benzyl-3-(2-methyloctyl-7-enoyl)oxazolidin-2-one. S4. Reduce 4-benzyl-3-(2-methyloctyl-7-enoyl)oxazolidin-2-one with NaBH4 to give 2-methyloctyl-7-en-1-ol; S5. 2-Methyloct-7-en-1-ol was protected with TBDPSCl to obtain tert-butyl(2-methyloct-7-en-1-yloxy)diphenylsilane; S6. p-tert-butyl(2-methyloct-7-en-1-yloxy)diphenylsilane is used to oxidize an olefin to an alcohol via a hydroboration oxidation reaction to give 8-tert-butyldiphenylsilyloxy-7-methyloct-1-ol. S7. 8-tert-butyldiphenylsilyloxy-7-methyloct-1-ol was sulfonated with TsCl to synthesize p-toluenesulfonic acid-8-tert-butyldiphenylsilyloxy-7-methyloctyl ester.

[0009] Preferably, when 4-benzyloxazolidin-2-one is (S)-4-benzyloxazolidin-2-one, step S7 yields S-configured 8-tert-butyldiphenylsilyloxy-7-methyloctyl p-toluenesulfonic acid.

[0010] Preferably, when 4-benzyloxazolidin-2-one is (R)-4-benzyloxazolidin-2-one, step S7 yields 8-tert-butyldiphenylsilyloxy-7-methyloctyl ester of p-toluenesulfonic acid with the R configuration.

[0011] A method for synthesizing 2,10-dimethyldodecyloxytert-butyldiphenylsilane based on 8-tert-butyldiphenylsilyloxy-7-methyloctyl toluenesulfonate includes the following steps: 2,10-Dimethyldodecyloxytert-butylsilylsilyl-7-methyloctyl ester of p-toluenesulfonic acid was prepared by nucleophilic substitution reaction with Grignard reagent, which was made from bromide and Mg.

[0012] A method for synthesizing 3,11-dimethyl-2,9-dicarbon-12-ene based on 2,10-dimethyl-1,9 ... A. 2,10-Dimethyldodecyloxytert-butyldiphenylsilane was deprotected with TBAF to obtain 2,10-dimethyldodecyl-1-ol; B. The hydroxyl group of 2,10-dimethyldodecyl-1-ol was converted to an aldehyde group by the Dess-Martin reaction, and then the carbon chain was extended by the Wittig reaction with bromo(heptadecyl)triphenylphosphine to synthesize 3,11-dimethyl-2,9-octadecan-12-ene.

[0013] A method for synthesizing 3,11-dimethylnonadec-12-ene from 3,11-dimethylnonadec-12-ene includes the following steps: reducing 3,11-dimethylnonadec-12-ene with Pd / C to synthesize 3,11-dimethylnonadec-12-ene.

[0014] A method for synthesizing 3,11-dimethylnonacontane based on 8-tert-butyldiphenylsilyloxy-7-methyloctyl p-toluenesulfonate includes the following steps: First, 2,10-dimethyldodecyloxytert-butylsilylsilyloxy-7-methyloctyl ester of p-toluenesulfonate was used as a raw material to synthesize 2,10-dimethyldodecyloxytert-butylsilylsilane. Then, using 2,10-dimethyldodecyloxytert-butyldiphenylsilane as a raw material, 3,11-dimethylnonadecano-12-ene was synthesized. Finally, 3,11-dimethylnonadecane was synthesized from 3,11-dimethylnonadecane.

[0015] Compared with the prior art, the beneficial technical effects of this application are as follows: In this application, 8-bromooctanoic acid is used as the starting material. It is first reacted with t-BuOK and 18-crown ether-6; then reacted with pentanoyl chloride to generate an anhydride, followed by acylation with 4-benzyloxazolidine-2-one; then diastereoselective methylation; then reduction with NaBH4; then hydroxyl protection using TBDPSCl; then hydroboration oxidation to oxidize the olefin to an alcohol; and finally sulfonation with TsCl to synthesize p-toluenesulfonate-8-tert-butyldiphenylsilyloxy-7-methyloctyl ester. The optical purity of the (S)-p-toluenesulfonate-8-tert-butyldiphenylsilyloxy-7-methyloctyl ester synthesized in this application reaches 98%, and the optical purity of the (R)-p-toluenesulfonate-8-tert-butyldiphenylsilyloxy-7-methyloctyl ester synthesized in this application also reaches 98%. Attached Figure Description

[0016] Figure 1 The liquid chromatogram of (S)-3,5-dinitrobenzoic acid 2-methyloct-7-en-1-yl ester; Figure 2 The liquid chromatogram of (R)-3,5-dinitrobenic acid 2-methyloct-7-en-1-yl ester. Detailed Implementation

[0017] Example 1: A method for synthesizing (S)-p-toluenesulfonic acid 8-tert-butyldiphenylsilyloxy-7-methyloctyl ester (as shown in formula (S)-10), the synthetic route of which is shown in the following reaction formula: ; The method for synthesizing (S)-8-tert-butyldiphenylsilyloxy-7-methyloctyl ester of p-toluenesulfonic acid (as shown in formula (S)-10) includes the following steps: S1. Under argon protection and at room temperature, potassium tert-butoxide (t-BuOK) (25.13 g, 224.0 mmol) and tetrahydrofuran (THF) (200 mL) were added to a 500 mL single-necked flask, followed by 8-bromooctanoic acid (as shown in Formula 2) (10.00 g, 44.8 mmol) to obtain the reaction system. Then, 18-crown ether-6 (4.14 g, 15.68 mmol) was dissolved in tetrahydrofuran (THF) (20 mL) and added to the reaction system to obtain the reaction solution. The reaction solution was heated to 66 °C and refluxed for 8 h. Then, the reaction solution was cooled to 0 °C, and under stirring, HCl solution with a molar concentration of 2 mol / L was added dropwise to the reaction solution until the pH of the reaction solution reached 2.0. The organic phase and the aqueous phase were then separated. The separated organic phase and the separated aqueous phase were extracted three times with ethyl acetate (EtOAc), with 50 mg of ethyl acetate (EtOAc) used in each extraction. mL, then the organic phases obtained from the three extractions were combined with the separated organic phases; then, the combined organic phases were washed with saturated NaCl solution (80 mL) and dried with anhydrous Na2SO4; then, the crude product was obtained by vacuum concentration. The crude product obtained in step S1 was purified by silica gel chromatography (petroleum ether / ethyl acetate 10:1) to obtain oct-7-enoic acid (6.37 g, yield 95%), which is a pale yellow oily substance. The structural formula of oct-7-enoic acid is shown in formula (3) in the reaction formula. The 1H NMR, 1C NMR, and high-resolution mass spectrometry results of oct-7-enoic acid are as follows: 1 H NMR (500MHz, CDCl3) δ 5.80 (ddt, J = 16.9, 10.2, 6.7 Hz, 1H), 5.00 (dq, J = 17.1, 1.8Hz, 1H), 4.94 (dq, J = 10.2, 1.5 Hz, 1H), 2.35 (t, J = 7.6 Hz, 2H), 2.09 –2.03 (m, 2H), 1.65 (q, J = 7.5 Hz, 2H), 1.43 – 1.34 (m, 4H); 13 C NMR (126 MHz, CDCl3) δ 180.55, 138.85, 114.59, 34.18, 33.64, 28.61, 24.62; HRMS (ESI, m / z):calculated for C8H 15 O2 + [M + H] +: 143.1001, found: 143.1003.

[0018] S2. Under argon protection and at -78°C, octyl-7-enoic acid (3.50 g, 24.61 mmol) and tetrahydrofuran (THF) (60 mL) were added to a 250 mL Shrek flask. Triethylamine Et3N (4.98 g, 49.22 mmol) and pivaloyl chloride (4.45 g, 36.92 mmol) were slowly added, and the mixture was stirred continuously at -78°C for 0.5 h to obtain a reaction mixture. The reaction mixture was then heated to room temperature and stirred for 1 h. Lithium chloride (3.65 g, 86.13 mmol) was then added, and the temperature was lowered again to -78°C. A tetrahydrofuran solution of (S)-4-benzyloxazolidine-2-one was then slowly added dropwise while maintaining the temperature at -78°C. The mixture was stirred at ℃ for 1 h, then the temperature was raised to room temperature and stirred continuously for 8 h. The tetrahydrofuran solution of (S)-4-benzyloxazolidine-2-one was obtained by mixing (S)-4-benzyloxazolidine-2-one (5.23 g, 29.53 mmol) and tetrahydrofuran (THF) (20 mL). The tetrahydrofuran solution of (S)-4-benzyloxazolidine-2-one is abbreviated as (S)-Boz (S)-4 in the reaction formula for the synthesis of (S)-p-toluenesulfonic acid 8-tert-butyldiphenylsilyloxy-7-methyloctyl ester. The chemical reaction was then quenched with 50 mL of water. The organic phase was then separated by extracting the aqueous phase three times with ethyl acetate (EtOAc), with 50 mL of ethyl acetate (EtOAc) used in each extraction. The organic phases obtained from the three extractions were then combined with the organic phase separated in step S2. The combined organic phases were then washed with saturated NaCl solution (80 mL), dried with anhydrous Na2SO4, and then concentrated under reduced pressure to obtain the crude product. The crude product obtained in step S2 was purified by silica gel chromatography (petroleum ether / ethyl acetate 30:1) to obtain a white solid substance (S)-4-benzyl-3-oct-7-enoyloxazolidine-2-one (7.05 g, 95% yield); in this application, the structural formula of (S)-4-benzyl-3-oct-7-enoyloxazolidine-2-one is shown in formula (S)-5 in the reaction formula. Specific rotation, 1H NMR, 1C NMR, and high-resolution mass spectrometry were performed on (S)-4-benzyl-3-oct-7-enoyloxazolidin-2-one. The results are as follows: [α] D 25 = + 44.29 (c 6.24, CHCl3); 1H NMR (500 MHz, CDCl3)δ 7.39 – 7.24 (m, 5H), 5.86 (ddt, J = 16.9, 10.2, 6.7 Hz, 1H), 5.08 – 4.98(m, 2H), 4.75 – 4.68 (m, 1H), 4.25 – 4.19 (m, 2H), 3.34 (dd, J = 13.4, 3.4Hz, 1H), 3.04 – 2.93 (m, 2H), 2.81 (dd, J = 13.4, 9.6 Hz, 1H), 2.14 – 2.09(m, 2H), 1.78 – 1.73 (m, 2H), 1.52 – 1.44 (m, 4H); 13 C NMR (125 MHz, CDCl3) δ173.54, 153.66, 139.03, 135.52, 129.61, 129.14, 127.53, 114.62, 66.36, 55.34,38.13, 35.67, 33.78, 28.82, 28.77, 24.29.; HRMS (ESI, m / z): calculated forC 18 H 24 NO3 + [M + H] + : 302.1686, found: 302.1689; S3. Under argon protection and at -78 °C, (S)-4-benzyl-3-oct-7-enoyloxazolidin-2-one (4.86 g, 16.12 mmol) and tetrahydrofuran (THF) (80 mL) were added to a 250 mL Shrek flask. Then, 12.1 mL of sodium bis(trimethylsilyl)amino was added dropwise over 30 minutes using a syringe pump. The sodium bis(trimethylsilyl)amino used in this application is an existing reagent, expressed as NaHMDS in the reaction formula. The specification of the sodium bis(trimethylsilyl)amino used in this application is sodium bis(trimethylsilyl)amino (2.0 M, solution in THF). After the addition was complete, the mixture was stirred at -78 °C for 1 hour. Then, iodomethane (5.01 mL, 80.60 mmol) was added dropwise over 1 hour using a syringe pump. After the addition was complete, the mixture was stirred at -78 °C for 8 hours. Finally, a saturated NH4Cl aqueous solution (50 mL) was used to react the iodomethane. (mL) quench chemical reactions; The organic phase was then separated by extracting the aqueous phase three times with ethyl acetate (EtOAc), with 50 mL of ethyl acetate (EtOAc) used in each extraction. The organic phases obtained from the three extractions were then combined with the organic phase separated in step S3. The combined organic phases were then washed with saturated NaCl solution (100 mL), dried with anhydrous Na2SO4, and then concentrated under reduced pressure to obtain the crude product. The crude product obtained in step S3 was then purified by silica gel chromatography (petroleum ether / ethyl acetate 20:1) to obtain a pale yellow oily substance (S)-4-benzyl-3-((S)-2-methyloctyl-7-enoyl)oxazolidin-2-one (4.42 g, 87% yield); the structural formula of (S)-4-benzyl-3-((S)-2-methyloctyl-7-enoyl)oxazolidin-2-one is shown in formula (S,S)-6 in the reaction formula; Specific rotation, 1H NMR, 1C NMR, and high-resolution mass spectrometry were performed on (S)-4-benzyl-3-((S)-2-methyloct-7-enoyl)oxazolidin-2-one. The results are as follows: [α] D 25 = + 65.00 (c 2.00, CHCl3); 1 H NMR(500 MHz, CDCl3) δ 7.33 – 7.20 (m, 5H), 5.79 (ddt, J = 16.9, 10.1, 6.7 Hz,1H), 5.03 – 4.89 (m, 2H), 4.71 – 4.63 (m, 1H), 4.22 – 4.14 (m, 2H), 3.71 (q,J = 6.8 Hz, 1H), 3.26 (dd, J = 13.4, 3.3 Hz, 1H), 2.77 (dd, J = 13.4, 9.6 Hz,1H), 2.05 (qt, J = 7.1, 1.5 Hz, 2H), 1.75 (ddt, J = 13.0, 8.7, 6.3 Hz, 1H), 1.45 – 1.30 (m, 5H), 1.22 (d, J = 6.8 Hz, 3H); 13 C NMR (125 MHz, CDCl3) δ139.17, 114.38, 68.45, 35.84, 33.87, 33.08, 29.28, 26.55, 16.69; HRMS (ESI, m / z): calculated for C 19 H 26 NO3+ [M + H] + : 316.1841, found: 316.1844; S4. Under argon protection and at 0 °C, (S)-4-benzyl-3-((S)-2-methyloctyl-7-enoyl)oxazolidin-2-one (3.10 g, 9.83 mmol) and tetrahydrofuran (THF) (30 mL) were added to a 100 mL single-necked flask. Then, an aqueous solution of NaBH4 was added dropwise over 0.5 h to obtain the reaction solution. The aqueous solution of NaBH4 was obtained by uniformly mixing NaBH4 (1.49 g, 39.32 mmol) and water (5 mL). After the addition was completed, the reaction solution was raised to room temperature and stirred continuously for 8 h. Then, the temperature was lowered to 0 °C, and under 0 °C and continuous stirring, hydrochloric acid with a molar concentration of 2 mol / L was added dropwise to acidify the reaction solution to pH 6. The organic and aqueous phases were then separated. The aqueous phase was extracted three times with ethyl acetate (EtOAc), with 50 mL of ethyl acetate (EtOAc) used in each extraction. The organic phases obtained from the three extractions were then combined with the organic phase separated in step S4. The combined organic phases were then washed sequentially with saturated NaHCO3 aqueous solution (50 mL) and saturated NaCl aqueous solution (50 mL). The washed organic phases were then dried with anhydrous Na2SO4 and concentrated under reduced pressure to obtain the crude product. The crude product obtained in step S4 was purified by silica gel chromatography (petroleum ether / ethyl acetate 20:1) to obtain a colorless oily substance (S)-2-methyloct-7-en-1-ol (1.33 g, 95% yield); the structural formula of (S)-2-methyloct-7-en-1-ol is shown in formula (S)-7. Specific rotation, 1H NMR, 1C NMR, and high-resolution mass spectrometry were performed on (S)-2-methyloct-7-en-1-ol. The results are as follows: [α] D 25 = − 12.87 (c 1.37, CHCl3); 1H NMR (500 MHz, CDCl3) δ 5.81(ddt, J = 17.0, 10.2, 6.7 Hz, 1H), 5.00 (dq, J = 17.1, 1.8 Hz, 1H), 4.94(ddt, J = 10.1, 2.3, 1.3 Hz, 1H), 3.51 (dd, J = 10.5, 5.8 Hz, 1H), 3.42 (dd,J = 10.5, 6.5 Hz, 1H), 2.08 – 2.03 (m, 2H), 1.64 – 1.59 (m, 1H), 1.43 – 1.29(m, 6H), 1.15 – 1.09 (m, 1H), 0.92 (d, J = 6.7 Hz, 3H); 13 C NMR (125 MHz, CDCl3) δ 139.17, 114.38, 68.45, 35.84, 33.87, 33.08, 29.28, 26.55, 16.69; HRMS (ESI, m / z): calculated for C9H 19 O + [M + H] + : 143.1366, found: 143.1372; S5. Under argon protection and at 0°C, 4-dimethylaminopyridine (DMAP) (86.0 mg, 0.70 mmol), imidazole (599.0 mg, 8.80 mmol), and dichloromethane (DCM) (20 mL) were added to a 50 mL Shrek tube. Then, (S)-2-methyloct-7-en-1-ol (500.0 mg, 3.52 mmol) was slowly added. After thorough stirring, tert-butyldiphenylchlorosilane (TBDPSCl) (1.16 g, 4.22 mmol) was added under stirring. The mixture was then brought to room temperature and stirred for 24 h. The reaction was then quenched with water (5 mL). The organic and aqueous phases were then separated. The aqueous phase was then extracted three times with dichloromethane (DCM), with 5 mL of DCM used in each extraction. The organic phases obtained from the three extractions were then combined with the organic phase separated in step S5. The combined organic phases were then washed with saturated NaCl solution (10 mL), dried with anhydrous Na2SO4, and then concentrated under reduced pressure to obtain the crude product. The crude product obtained in step S5 was purified by silica gel chromatography (petroleum ether / ethyl acetate 20:1) to obtain a colorless oily substance (S)-tert-butyl(2-methyloct-7-en-1-yloxy)diphenylsilane (1.25 g, 93% yield); wherein, the structural formula of (S)-tert-butyl(2-methyloct-7-en-1-yloxy)diphenylsilane is shown in formula (S)-8. Specific rotation, 1H NMR, 1C NMR, and high-resolution mass spectrometry were performed on (S)-tert-butyl(2-methyloct-7-en-1-yloxy)diphenylsilane. The results are as follows: [α] D 25 = − 2.16 (c 1.11, CHCl3); 1 H NMR (500MHz, CDCl3) δ 7.69 – 7.66 (m, 4H), 7.43 – 7.35 (m, 6H), 5.81 (ddt, J = 16.9,10.1, 6.7 Hz, 1H), 5.00 (dq, J = 17.1, 1.8 Hz, 1H), 4.94 (ddt, J = 10.1, 2.3,1.3 Hz, 1H), 3.50 (dd, J = 6.0 Hz, 1H), 3.44 (dd, J = 9.8, 6.3 Hz, 1H), 2.03(q, J = 7.1 Hz, 2H), 1.68 – 1.63 (m, 1H), 1.47 – 1.22 (m, 6H), 1.06 (s, 9H), 0.92 (d, J = 6.7 Hz, 3H); 13 C NMR (125 MHz, CDCl3) δ 139.33, 135.77, 134.26,129.61, 127.69, 114.30, 69.04, 35.80, 33.93, 33.11, 29.34, 27.02, 26.59,19.47, 17.02; HRMS (ESI, m / z): calculated for C 25 H 36 OSiNa + [M + Na] + : 403.2438, found: 403.2441; S6. Under argon protection and at room temperature, add ( ) to a 100 mL three-necked flask. S1.16 g (3.05 mmol) of tert-butyl(2-methyloct-7-en-1-yloxy)diphenylsilane and 20 mL of tetrahydrofuran (THF) were added. After thorough stirring, 18.3 mL of a tetrahydrofuran solution of 9-boronbicyclo[3.3.1]nonane (9-BBN, monomer, CAS: 280-64-8) with a molar concentration of 0.5 mol / L was slowly added to obtain the reaction system. The reaction system was stirred continuously for 12 h, then cooled to 0 °C, and 6.1 mL of NaOH solution with a molar concentration of 3 mol / L was added to the reaction system at 0 °C. After stirring continuously for 30 min, the temperature was lowered to -20 °C, and then 6.1 mL of H2O2 solution (H2O2 mass concentration in H2O2 solution was 30%) was slowly added. Then, the mixture was heated to room temperature and stirred continuously for 3 h. Then, quenching was performed using 10 mL of saturated NH4Cl aqueous solution. The organic and aqueous phases were then separated. The aqueous phase was extracted three times with ethyl acetate (EtOAc), with 20 mL of ethyl acetate (EtOAc) used in each extraction. The organic phases obtained from the three extractions were then combined with the organic phase separated in step S6. The combined organic phases were then washed with 20 mL of saturated NaCl solution and dried with anhydrous Na2SO4. The crude product was then concentrated under reduced pressure. The crude product obtained in step S6 was then purified by silica gel chromatography (petroleum ether / ethyl acetate 5:1) to obtain a colorless oily substance (S)-8-tert-butyldiphenylsilyloxy-7-methyloct-1-ol (1.11 g, 91% yield), wherein the structural formula of (S)-8-tert-butyldiphenylsilyloxy-7-methyloct-1-ol is shown in formula (S)-9. Specific rotation, 1H NMR, 1C NMR, and high-resolution mass spectrometry were performed on (S)-8-tert-butyldiphenylsilyloxy-7-methyloct-1-ol. The results are as follows: [α] D 25 = − 0.61 (c 1.31, CHCl3); 1 H NMR (500MHz, CDCl3) δ 7.61 – 7.57 (m, 4H), 7.36 – 7.28 (m, 6H), 3.55 (t, J = 6.7 Hz, 2H), 3.43 – 3.41 (m, 1H), 3.36 (dd, J = 9.8, 6.4 Hz, 1H), 1.55 – 1.34 (m,6H), 1.28 – 1.16 (m, 6H), 0.98 (s, 9H), 0.84 (d, J = 6.7 Hz, 3H);13 C NMR (125MHz, CDCl3) δ 135.76, 134.25, 129.60, 127.68, 69.05, 63.21, 35.81, 33.19,32.91, 29.82, 27.03, 27.01, 25.83, 19.46, 17.02; HRMS (ESI, m / z): calculated for C 25 H 39 O2Si + [M + H] + : 399.2648, found: 399.2652; S7. Under argon protection and at room temperature, triethylamine (330.0 mg, 3.26 mmol), 4-dimethylaminopyridine (DMAP) (100.0 mg, 0.82 mmol), and dichloromethane (DCM) (20 mL) were added to a 100 mL Shrek flask. After thorough stirring, (S)-8-tert-butyldiphenylsilyloxy-7-methyloct-1-ol (650.0 mg, 1.63 mmol) was slowly added. Then, TsCl-DCM solution was slowly added, which was obtained by dissolving p-toluenesulfonyl chloride (TsCl) (467.0 mg, 2.45 mmol) in dichloromethane (DCM) (5 mL). The mixture was then stirred at room temperature for 18 h. The reaction was then quenched with water (15 mL). The organic phase was then separated, and the aqueous phase was extracted three times with dichloromethane (DCM), with 10 mL of DCM used in each extraction. The organic phases obtained from the three extractions were then combined with the organic phase separated in step S7. The combined organic phases were then washed with saturated NaCl solution (20 mL), dried with anhydrous Na2SO4, and then concentrated under reduced pressure to obtain the crude product.

[0019] The crude product obtained in step S7 was purified by silica gel chromatography (petroleum ether / ethyl acetate 2:1) to obtain a colorless oily substance (S)-8-tert-butyldiphenylsilyloxy-7-methyloctyl p-toluenesulfonic acid (856.0 mg, 95% yield); wherein, the structural formula of (S)-8-tert-butyldiphenylsilyloxy-7-methyloctyl p-toluenesulfonic acid is shown in formula (S)-10. Specific rotation, 1H NMR, 1C NMR, and high-resolution mass spectrometry were performed on (S)-8-tert-butyldiphenylsilyloxy-7-methyloctyl ester of p-toluenesulfonic acid. The results are as follows: [α] D 25= − 5.83 (c 1.92, CHCl3); 1 H NMR(500 MHz, CDCl3) δ 7.71 (d, J = 8.2 Hz, 2H), 7.61 – 7.54 (m, 4H), 7.36 – 7.23(m, 8H), 3.93 (t, J = 6.5 Hz, 2H), 3.40 (d, J = 7.1 Hz, 1H), 3.34 (dd, J =9.8, 6.4 Hz, 1H), 2.36 (s, 3H), 1.56 – 1.48 (m, 4H), 1.33 – 1.26 (m, 1H),1.20 – 1.06 (m, 6H), 0.97 (s, 9H), 0.81 (d, J = 6.7 Hz, 3H); 13 C NMR (125 MHz,CDCl3) δ 144.74, 135.74, 134.20, 133.34, 129.92, 129.62, 128.00, 127.68,70.82, 68.97, 35.74, 33.08, 29.32, 28.92, 27.00, 26.81, 25.42, 21.76, 19.44,16.98;HRMS (ESI, m / z): calculated for C 32 H 45 O4SSi + [M + H] + : 553.2737‬, found:553.2739; In this application, it is not possible to directly determine the ee (enantiomeric excess) value of (S)-8-tert-butyldiphenylsilyloxy-7-methyloctyl ester (as shown in (S)-10), while (S)-2-methyloct-7-en-1-ol (as shown in (S)-7) is a precursor for the synthesis of (S)-8-tert-butyldiphenylsilyloxy-7-methyloctyl ester (as shown in (S)-10). Therefore, in order to determine the ee (enantiomeric excess) value of (S)-8-tert-butyldiphenylsilyloxy-7-methyloctyl ester (as shown in (S)-10), The optical purity of (S)-2-methyloct-7-en-1-ol (as shown in (S)-7) is determined by this application based on the esterification derivatization of (S)-2-methyloct-7-en-1-ol (as shown in (S)-7) with 3,5-dinitrobenzoyl chloride (DNBC) followed by optical testing. In other words, this application first esterifies (S)-2-methyloct-7-en-1-ol (as shown in (S)-7) using 3,5-dinitrobenzoyl chloride (DNBC), and then determines the optical purity (ee) of the esterified derivatives of (S)-2-methyloct-7-en-1-ol by chiral HPLC. The optical purity of (S)-8-tert-butyldiphenylsilyloxy-7-methyloctyl ester (as shown in (S)-10) can be obtained by measuring the optical purity of (S)-2-methyloct-7-en-1-ol (as shown in (S)-7) via esterification derivatization using 3,5-dinitrobenzoyl chloride (DNBC), is shown below: ;

[0020] The reaction of (S)-2-methyloct-7-en-1-ol with 3,5-dinitrobenzoyl chloride (DNBC) involved the following steps: (S)-2-methyloct-7-en-1-ol (as shown in (S)-7) (1.00 g, 7.03 mmol) was dissolved in dichloromethane (DCM) (20 mL) at 0 °C, followed by the dropwise addition of triethylamine (1.47 mL, 10.55 mmol). After stirring for 10 minutes, a solution of 3,5-dinitrobenzoyl chloride (DNBC) (2.11 g, 9.14 mmol, CAS: 99-33-2) in DCM (5 mL) was added dropwise to obtain the reaction solution. The reaction solution was then brought to room temperature and stirred continuously for 8 hours. The temperature was then lowered to 0 °C, and the solution was then reacted with a saturated aqueous NH4Cl solution (10 mL). The reaction was quenched using 10 mL of dichloromethane (DCM). After quenching, the organic and aqueous phases were separated. The aqueous phase was then extracted three times with 10 mL of DCM each time. The extracted organic phases were then combined with the separated organic phases. The combined organic phases were washed with 20 mL of saturated NaCl solution, dried with anhydrous Na2SO4, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel chromatography (petroleum ether / ethyl acetate 10:1) to obtain a pale yellow solid (S)-3,5-dinitrobenzoic acid 2-methyloct-7-en-1-yl ester (as shown in (S)-15) (2.08 g, 88% yield). The (S)-3,5-dinitrobenzoic acid 2-methyloct-7-en-1-yl ester (as shown in (S)-15) is a derivative of (S)-2-methyloct-7-en-1-ol.

[0021] The specific rotation, 1H NMR, 1C NMR, and high-resolution mass spectrometry of (S)-3,5-dinitrobenzoic acid 2-methyloct-7-en-1-yl ester (as shown in (S)-15) were determined, and the results are as follows: [α] D 25 = + 0.81 (c 2.46, CHCl3). 1H NMR (500 MHz, CDCl3) δ 9.14 (t, J = 2.1 Hz, 1H), 9.07 (d, J = 2.2Hz, 2H), 5.72 (ddt, J = 16.9, 10.1, 6.7 Hz, 1H), 4.91 (dq, J = 17.1, 1.7 Hz,1H), 4.85 (ddt, J = 10.1, 2.2, 1.2 Hz, 1H), 4.27 (dd, J = 10.7, 5.9 Hz, 1H), 4.17 (dd, J = 10.7, 6.9 Hz, 1H), 2.01 – 1.92 (m, 3H), 1.45 – 1.24 (m, 6H),0.98 (d, J = 6.7 Hz, 3H). 13 C NMR (126 MHz, CDCl3) δ 162.67, 148.79, 138.86,134.25, 129.45, 122.40, 114.54, 71.85, 33.73, 33.28, 32.71, 29.07, 26.35,17.05. HRMS (ESI, m / z): calculated for C 16 H 26 N2O6 + [M + H] + : 337.1330, found: 337.1334.

[0022] The optical purity of (S)-2-methyloct-7-en-1-ol derivatives (as shown in formula (S)-15) was determined by chiral high-performance liquid chromatography (HPLC). The chromatographic column type was Daicel Chiralcel OD-H column, the mobile phase was n-hexane / i-propanol = 97:3, the flow rate was 1.0 mL / min, and the wavelength was λ = 254 nm. The HPLC chromatogram of the (S)-2-methyloct-7-en-1-ol derivatives was obtained as follows: Figure 1 As shown.

[0023] from Figure 1As can be seen, the derivative of (S)-2-methyloct-7-en-1-ol (as shown in formula (S)-15) has two peaks. The peak area percentage at 24.943 min is 0.8608%, and the peak area percentage at 27.075 min is 99.1392%. Calculations show that the ee value of the derivative of (S)-2-methyloct-7-en-1-ol is 98%. That is to say, the ee value of (S)-8-tert-butyldiphenylsilyloxy-7-methyloctyl ester of p-toluenesulfonate is 98%.

[0024] Example 2: (R)-8-tert-butyldiphenylsilyloxy-7-methyloctyl ester of p-toluenesulfonate (as shown in formula ( R The synthetic method shown in Figure 10 is as follows, and the synthetic route is shown in the following reaction formula: ; Comparing the reaction formulas of Example 1 and Example 2, it can be found that the only difference between Example 2 and Example 1 is that: (1) In step S2, Example 2 adopts ( R )-Boz( R )-4 replaces ( in Example 1) S )-Boz( S )-4; In Example 2 ( R )-Boz ( R (R)-4-benzyloxazolidin-2-one in tetrahydrofuran solution. R )-Boz ( R )-4 is composed of ( R The mixture of 4-benzyloxazolidin-2-one (5.23 g, 29.53 mmol) and tetrahydrofuran (THF) (20 mL) was homogeneous. In Example 2, step S2 yielded a white solid (R)-4-benzyl-3-oct-7-enoyloxazolidin-2-one (7.12 g, 96% yield); wherein the structural formula of (R)-4-benzyl-3-oct-7-enoyloxazolidin-2-one is shown in formula (R)-5.

[0025] Specific rotation, 1H NMR, 1C NMR, and high-resolution mass spectrometry were performed on (R)-4-benzyl-3-oct-7-enoyloxazolidin-2-one. The results are as follows: [α] D 25 = − 43.07 (c 9.71, CHCl3); 1H NMR (500 MHz, CDCl3)δ 7.35 – 7.20 (m, 5H), 5.81 (ddt, J = 16.9, 10.1, 6.7 Hz, 1H), 5.01 (dd, J =17.2, 1.9 Hz, 1H), 4.94 (dd, J = 10.3, 2.1 Hz, 1H), 4.69 – 4.64 (m, 1H), 4.20– 4.14 (m, 2H), 3.29 (dd, J = 13.4, 3.3 Hz, 1H), 2.99 – 2.87 (m, 2H), 2.77(dd, J = 13.4, 9.6 Hz, 1H), 2.10 – 2.05 (m, 2H), 1.73 – 1.67 (m, 2H), 1.47 –1.38 (m, 4H); 13 C NMR (125 MHz, CDCl3) δ 173.42, 153.55, 138.93, 135.42,129.51, 129.04, 127.42, 114.53, 66.25, 55.23, 38.01, 35.57, 33.68, 28.72,28.66, 24.18; HRMS (ESI, m / z): calculated for C 18 H 24 NO3 + [M + H] + : 302.1687, found: 302.1671.

[0026] (2) In step S3, in Example 2, (R)-4-benzyl-3-oct-7-enoyloxazolidine-2-one (3.52 g, 11.68 mmol) was used instead of (S)-4-benzyl-3-oct-7-enoyloxazolidine-2-one (4.86 g, 16.12 mmol) used in Example 1; in Example 2, the amount of sodium bis(trimethylsilyl)amino was 8.76 mL; in Example 2, the amount of iodomethane was 3.64 mL. In Example 2, step S3 yielded a pale yellow oily substance (R)-4-benzyl-3-((R)-2-methyloctyl-7-enoyl)oxazolidin-2-one (3.35 g, 91% yield), the structural formula of which is the same as shown in formula (R,R)-6; Specific rotation, 1H NMR, 1C NMR, and high-resolution mass spectrometry were performed on (R)-4-benzyl-3-((R)-2-methyloct-7-enoyl)oxazolidin-2-one. The results are as follows: [α] D 25 = − 49.66 (c 9.44, CHCl3); 1 H NMR(500 MHz, CDCl3) δ 7.34 – 7.21 (m, 5H), 5.79 (ddt, J = 16.9, 10.2, 6.7 Hz, 1H), 4.99 (dd, J = 17.1, 1.9 Hz, 1H), 4.94 – 4.91 (m, 1H), 4.69 – 4.65 (m,1H), 4.20 – 4.15 (m, 2H), 3.70 (q, J = 6.8 Hz, 1H), 3.26 (dd, J = 13.3, 3.3Hz, 1H), 2.77 (dd, J = 13.4, 9.6 Hz, 1H), 2.07 – 2.02 (m, 2H), 1.78 – 1.72(m, 1H), 1.42 – 1.30 (m, 5H), 1.22 (d, J = 6.8 Hz, 3H); 13 C NMR (125 MHz, CDCl3) δ 177.32, 153.13, 138.90, 135.42, 129.53, 128.99, 127.40, 114.49, 66.09, 55.41, 37.97, 37.75, 33.66, 33.29, 28.94, 26.76, 17.43; HRMS (ESI, m / z): calculated for C 19 H 26 NO3 + [M + H] + : 316.1841, found: 316.1847; (3) In step S4, in Example 2, (R)-4-benzyl-3-((R)-2-methyloctyl-7-enoyl)oxazolidin-2-one (3.50 g, 11.10 mmol) was used instead of (S)-4-benzyl-3-((S)-2-methyloctyl-7-enoyl)oxazolidin-2-one (3.10 g, 9.83 mmol) in Example 1; the aqueous solution of NaBH4 used in Example 2 was obtained by mixing NaBH4 (1.68 g, 44.4 mmol) and water (5 mL) evenly. In Example 2, step S4 yielded a colorless oily substance (R)-2-methyloct-7-en-1-ol (1.48 g, 95% yield); wherein the structural formula of (R)-2-methyloct-7-en-1-ol is as shown in formula (R)-7. Specific rotation, 1H NMR, 1C NMR, and high-resolution mass spectrometry were performed on (R)-2-methyloct-7-en-1-ol. The results are as follows: [α] D 25 = + 11.71 (c 1.95, CHCl3); 1 H NMR (500 MHz, CDCl3) δ 5.81(ddt, J = 16.9, 10.2, 6.7 Hz, 1H), 5.00 (dq, J = 17.2, 1.7 Hz, 1H), 4.94(ddt, J = 10.1, 2.1, 1.2 Hz, 1H), 3.51 (dd, J = 10.5, 5.8 Hz, 1H), 3.42 (dd,J = 10.5, 6.5 Hz, 1H), 2.08 – 2.04 (m, 2H), 1.64 – 1.59 (m, 2H), 1.40 – 1.29(m, 5H), 1.14 – 1.08 (m, 1H), 0.92 (d, J = 6.7 Hz, 3H); 13 C NMR (125 MHz, CDCl3) δ 139.20, 114.41, 68.52, 35.87, 33.88, 33.10, 29.31, 26.58, 16.71; HRMS (ESI, m / z): calculated for C9H 19 O + [M + H] + : 143.1366, found: 143.1369.

[0027] (4) In step S5, (R)-2-methyloct-7-en-1-ol is used in Example 2 to replace (S)-2-methyloct-7-en-1-ol in Example 1; the amount of (R)-2-methyloct-7-en-1-ol used in Example 2 is the same as the amount of (S)-2-methyloct-7-en-1-ol used in Example 1. In Example 2, step S5 yielded a colorless oily substance (R)-tert-butyl(2-methyloct-7-en-1-yloxy)diphenylsilane (1.22 g, 91% yield); wherein the structural formula of (R)-tert-butyl(2-methyloct-7-en-1-yloxy)diphenylsilane is as shown in formula (R)-8. Specific rotation, 1H NMR, 1C NMR, and high-resolution mass spectrometry were performed on (R)-tert-butyl(2-methyloct-7-en-1-yloxy)diphenylsilane. The results are as follows: [α] D 25 = + 2.87 (c 1.11, CHCl3); 1 H NMR (500MHz, CDCl3) δ 7.59 (dt, J = 6.7, 1.6 Hz, 4H), 7.31 (ddd, J = 14.1, 7.6, 6.0Hz, 6H), 5.77 – 5.67 (m, 1H), 4.91 (dt, J = 17.1, 1.8 Hz, 1H), 4.85 (ddt, J =10.2, 2.2, 1.2 Hz, 1H), 3.43 (dd, 1H), 3.36 (dd, J = 9.8, 6.3 Hz, 1H), 1.95(q, J = 7.1 Hz, 2H), 1.56 (q, J = 6.5 Hz, 1H), 1.41 – 1.10 (m, 6H), 0.97 (s,9H), 0.83 (d, J = 6.7 Hz, 3H); 13 C NMR (125 MHz, CDCl3) δ 139.33, 135.77,134.26, 129.61, 127.69, 114.30, 69.04, 35.80, 33.93, 33.11, 29.34, 27.02,26.59, 19.47, 17.02; HRMS (ESI, m / z): calculated for C 25 H 36 OSiNa + [M + Na] + :403.2437, found: 403.2432; (5) In step S6, in Example 2, (S)-tert-butyl(2-methyloct-7-en-1-yloxy)diphenylsilane (as shown in formula (S)-8) is used to replace the (S)-tert-butyl(2-methyloct-7-en-1-yloxy)diphenylsilane in Example 1. R (S)-tert-butyl(2-methyloct-7-en-1-yloxy)diphenylsilane; In this Example 2, the amount of (S)-tert-butyl(2-methyloct-7-en-1-yloxy)diphenylsilane used was 1.08 g, the amount of tetrahydrofuran solution of 9-boronbicyclo[3.3.1]nonane (9-BBN, monomer, CAS: 280-64-8) used was 17.04 mL, the amount of NaOH solution used was 5.7 mL, and the amount of H2O2 solution used was 5.7 mL; In Example 2, step S6 yielded a colorless oily substance (R)-8-tert-butyldiphenylsilyloxy-7-methyloct-1-ol (as shown in formula (R)-9) (1.08 g, 95% yield). Specific rotation, 1H NMR, 1C NMR, and high-resolution mass spectrometry were performed on (R)-8-tert-butyldiphenylsilyloxy-7-methyloct-1-ol. The results are as follows: [α] D 25 = + 2.66 (c 1.95, CHCl3); 1 H NMR (500MHz, CDCl3) δ 7.61 – 7.57 (m, 4H), 7.36 – 7.28 (m, 6H), 3.55 (t, J = 6.7 Hz, 2H), 3.43 (dd, J = 9.8, 5.7 Hz, 1H), 3.36 (dd, J = 9.8, 6.3 Hz, 1H), 1.72 –1.44 (m, 4H), 1.39 – 1.35 (m, 2H), 1.26 – 1.14 (m, 6H), 0.98 (s, 9H), 0.84(d, J = 6.8 Hz, 3H); 13 C NMR (125 MHz, CDCl3) δ 135.77, 134.30, 129.61, 127.69,69.08, 63.23, 35.83, 33.22, 32.93, 29.83, 27.03, 25.84, 19.47, 17.03; HRMS(ESI, m / z): calculated for C 25 H 39 O2Si + [M + H] + : 399.2649, found: 399.2652.

[0028] (6) In step S7, in Example 2, (R)-8-tert-butyldiphenylsilyloxy-7-methyloct-1-ol (570.0 mg, 1.43 mmol) was used instead of (S)-8-tert-butyldiphenylsilyloxy-7-methyloct-1-ol (650.0 mg, 1.63 mmol); in Example 2, the amount of triethylamine was 289.0 mg, the amount of 4-dimethylaminopyridine DMAP was 88.0 mg, and the amount of p-toluenesulfonyl chloride TsCl was 409.0 mg; In Example 2, step S7 yielded a colorless oily substance (R)-p-toluenesulfonic acid-8-tert-butyldiphenylsilyloxy-7-methyloctyl ester (735.0 mg, 93% yield); wherein the structural formula of (R)-p-toluenesulfonic acid-8-tert-butyldiphenylsilyloxy-7-methyloctyl ester is shown in formula (R)-10. Specific rotation, 1H NMR, 1C NMR, and high-resolution mass spectrometry were performed on (R)-8-tert-butyldiphenylsilyloxy-7-methyloctyl ester. The results are as follows: [α] D 25 = + 3.28 (c 2.69, CHCl3); 1 H NMR(500 MHz, CDCl3) δ 7.71 (d, J = 8.3 Hz, 2H), 7.61 – 7.54 (m, 4H), 7.36 – 7.23(m, 8H), 3.93 (t, J = 6.5 Hz, 2H), 3.43 – 3.39 (m, 1H), 3.34 (dd, J = 9.8, 6.4 Hz, 1H), 2.36 (s, 3H), 1.53 (ddt, J = 14.0, 8.7, 4.3 Hz, 4H), 1.31 – 1.25 (m, 1H), 1.19 – 1.06 (m, 6H), 0.97 (s, 9H), 0.82 (d, J = 6.7 Hz, 3H); 13 C NMR(125 MHz, CDCl3) δ 144.74, 135.74, 134.20, 133.35, 129.92, 129.62, 128.01,127.69, 70.82, 68.97, 35.75, 33.09, 29.33, 28.92, 27.00, 26.82, 25.43, 21.76,19.44, 16.99; HRMS (ESI, m / z): calculated for C 32 H 45 O4SSi + [M + H] + : 553.2737, found: 553.2739.

[0029] In this application, it is not possible to directly determine the ee (enantiomeric excess) value of (R)-p-toluenesulfonic acid 8-tert-butyldiphenylsilyloxy-7-methyloctyl ester (as shown in (R)-10), while (R)-2-methyloct-7-en-1-ol (as shown in (R)-7) is a precursor for the synthesis of (R)-p-toluenesulfonic acid 8-tert-butyldiphenylsilyloxy-7-methyloctyl ester (as shown in (R)-10). Therefore, in order to determine the ee (enantiomeric excess) value of (R)-p-toluenesulfonic acid 8-tert-butyldiphenylsilyloxy-7-methyloctyl ester, the following method is used: Regarding optical purity, this application is based on the esterification derivatization of (R)-2-methyloct-7-en-1-ol (as shown in (R)-7) with 3,5-dinitrobenzoyl chloride (DNBC) followed by optical testing. That is, this application first esterifies and derivatizes (R)-2-methyloct-7-en-1-ol (as shown in (R)-7) using 3,5-dinitrobenzoyl chloride (DNBC), and then determines the optical purity (i.e., ee value) of the esterified derivative of (R)-2-methyloct-7-en-1-ol by chiral HPLC, thereby obtaining the optical purity of (R)-8-tert-butyldiphenylsilyloxy-7-methyloctyl ester of p-toluenesulfonic acid (as shown in (R)-10). The reaction pathway for the esterification derivatization of (R)-2-methyloct-7-en-1-ol (as shown in (R)-7) using 3,5-dinitrobenzoyl chloride (DNBC) is as follows: ;

[0030] The reaction of (R)-2-methyloct-7-en-1-ol with 3,5-dinitrobenzoyl chloride (DNBC) involves the following steps: At 0°C, (R)-2-methyloct-7-en-1-ol (as shown in (R)-7) (1.00 g, 7.03 mmol) was dissolved in dichloromethane (DCM) (20 mL), followed by the dropwise addition of triethylamine (1.47 mL, 10.55 mmol). After stirring for 10 minutes, a solution of 3,5-dinitrobenzoyl chloride (DNBC) (2.11 g, 9.14 mmol, CAS: 99-33-2) in DCM (5 mL) was added dropwise to obtain the reaction solution. The reaction solution was then brought to room temperature and stirred continuously for 8 hours. The temperature was then lowered to 0°C, and the reaction solution was then subjected to a saturated aqueous solution of NH4Cl (10... The reaction was quenched using 10 mL of dichloromethane (DCM). After quenching, the organic and aqueous phases were separated. The aqueous phase was then extracted three times with 10 mL of DCM each time. The extracted organic phases were then combined with the separated organic phases. The combined organic phases were washed with 20 mL of saturated NaCl solution, dried with anhydrous Na2SO4, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel chromatography (petroleum ether / ethyl acetate 10:1) to obtain a pale yellow solid (R)-3,5-dinitrobenzoic acid 2-methyloct-7-en-1-yl ester (as shown in (R)-15) (2.15 g, 91% yield). The (R)-3,5-dinitrobenzoic acid 2-methyloct-7-en-1-yl ester (as shown in (R)-15) is a derivative of (R)-2-methyloct-7-en-1-ol.

[0031] The specific rotation, 1H NMR, 1C NMR, and high-resolution mass spectrometry of (R)-3,5-dinitrobenzoic acid 2-methyloct-7-en-1-yl ester (as shown in (R)-15) were determined, and the results are as follows: [α] D 25 = + 0.75 (c 1.07, CHCl3). 1H NMR (500 MHz, CDCl3) δ 9.16 (t, J = 2.2 Hz, 1H), 9.08 (d, J = 2.2Hz, 2H), 5.73 (ddt, J = 16.9, 10.1, 6.7 Hz, 1H), 4.92 (dq, J = 17.1, 1.8 Hz,1H), 4.87 (dt, J = 10.2, 1.6 Hz, 1H), 4.29 – 4.25 (m, 1H), 4.17 (dd, J =10.7, 6.9 Hz, 1H), 2.02 – 1.92 (m, 3H), 1.43 – 1.27 (m, 6H), 0.98 (d, J = 6.8Hz, 3H). 13 C NMR (126 MHz, CDCl3) δ 162.70, 148.83, 138.89, 134.29, 129.50,122.45, 114.60, 71.89, 33.76, 33.32, 32.74, 29.11, 26.38, 17.08. HRMS (ESI,m / z): calculated for C 16 H 26 N2O6 + [M + H] + : 337.1329, found: 337.1327; The optical purity of (R)-2-methyloct-7-en-1-ol derivatives (as shown in formula (R)-15) was determined by chiral high-performance liquid chromatography (HPLC). The chromatographic column type was Daicel Chiralcel OD-H column, the mobile phase was n-hexane / i-propanol = 97:3, the flow rate was 1.0 mL / min, and the wavelength was λ = 254 nm. The HPLC chromatogram of the (R)-2-methyloct-7-en-1-ol derivatives was obtained as follows: Figure 2 As shown.

[0032] from Figure 2As can be seen, the derivative of (R)-2-methyloct-7-en-1-ol (as shown in formula (R)-15) has two peaks. The peak area percentage at 24.372 min is 98.9745%, and the peak area percentage at 27.269 min is 1.0255%. Calculations show that the ee value of the derivative of (R)-2-methyloct-7-en-1-ol is 98%. That is to say, the ee value of (R)-8-tert-butyldiphenylsilyloxy-7-methyloctyl ester of p-toluenesulfonate is 98%.

[0033] Example 3: A method for synthesizing (2S,10S)-2,10-dimethyldodecyloxytert-butyldiphenylsilane (as shown in formula (S)-10) using (S)-p-toluenesulfonic acid 8-tert-butyldiphenylsilyloxy-7-methyloctyl ester (as shown in formula (S)-10) S 10 S The method shown in Figure 12 has a synthetic route as shown in the following reaction formula: ; In this third embodiment, the method for synthesizing (2S,10S)-2,10-dimethyldodecyloxytert-butyldiphenylsilane using (S)-p-toluenesulfonic acid 8-tert-butyldiphenylsilyloxy-7-methyloctyl ester (as shown in formula (S)-10) includes the following steps: 1) Preparation of a tetrahydrofuran solution of (S)-2-methylbutylmagnesium bromide includes the following steps: Under argon protection and at room temperature, Mg (280.0 mg, 11.2 mmol) is added to a 25 mL three-necked flask equipped with a condenser, followed by the addition of tetrahydrofuran (THF) (7.5 mL) and iodine (100 mg), and then 0.23 g of (S)-1-bromo-2-methylbutane (99% ee, as shown in formula (S)-11, CAS 90719-32-7); then, the mixture is heated to 60 °C to initiate the reaction, and then 0.9 g of (S)-1-bromo-2-methylbutane is slowly added dropwise to obtain the reaction solution; the reaction solution is heated to reflux and stirred continuously for 0.5 h; then, the mixture is cooled to room temperature to obtain a tetrahydrofuran solution of (S)-2-methylbutylmagnesium bromide. 2) At -70 °C, (S)-p-toluenesulfonic acid 8-tert-butyldiphenylsilyloxy-7-methyloctyl ester (1.18 g, 2.14 mmol) and tetrahydrofuran (THF) (10 mL) were added to a 50 mL Shrek flask, followed by 6.4 mL of a tetrahydrofuran solution of Li2CuCl4 (0.1 mol / L). After thorough stirring, 7.5 mL of the tetrahydrofuran solution of (S)-2-methylbutylmagnesium bromide prepared in step 1) was slowly added dropwise. The mixture was stirred continuously at -70 °C for 1 h, then heated to room temperature and stirred overnight. The reaction was then quenched with saturated NH4Cl aqueous solution (15 mL). After quenching the reaction, the organic phase and the aqueous phase were separated. The aqueous phase was extracted three times with ethyl acetate (EtOAc), with 10 mL of ethyl acetate (EtOAc) used in each extraction. The organic phases obtained from the three extractions were then combined with the organic phase separated in step 3). The combined organic phases were then washed with saturated NaCl solution (20 mL), dried with anhydrous Na2SO4, and then concentrated under reduced pressure to obtain the crude product. The crude product obtained in step 3) was purified by silica gel chromatography (petroleum ether) to give a colorless oily substance (2S,10S)-2,10-dimethyldodecyloxytert-butyldiphenylsilane (as shown in formula (2S,10S)-12) (843.0 mg, 87% yield). Specific rotation, 1H NMR, 1C NMR, and high-resolution mass spectrometry were performed on (2S,10S)-2,10-dimethyldodecyloxytert-butyldiphenylsilane. The results are as follows: [α] D 25 = + 2.75 (c 1.75, CHCl3); 1 H NMR (500MHz, CDCl3) δ 7.69 (dt, J = 6.8, 1.6 Hz, 4H), 7.45 – 7.36 (m, 6H), 3.53 (dd,J = 9.8, 5.7 Hz, 1H), 3.45 (dd, J = 9.8, 6.4 Hz, 1H), 1.68 – 1.63 (m, 1H),1.46 – 1.40 (m, 1H), 1.38 – 1.17 (m, 14H), 1.16 – 1.10 (m, 2H), 1.07 (s, 9H),0.93 (d, J = 6.7 Hz, 3H), 0.90 – 0.85 (m, 6H); 13C NMR (125 MHz, CDCl3) δ135.79, 134.34, 129.60, 127.69, 69.13, 36.81, 35.87, 34.57, 33.31, 30.19,30.12, 29.86, 29.67, 27.29, 27.13, 27.05, 19.49, 19.39, 17.07, 11.57; HRMS(ESI, m / z): calculated for C 30 H 49 OSi + [M + H] + : 453.3481, found: 453.3484; Example 4: A method for synthesizing (2S,10R)-2,10-dimethyldodecyloxytert-butyldiphenylsilane (as shown in formula (2S)-10) using (S)-p-toluenesulfonic acid 8-tert-butyldiphenylsilyloxy-7-methyloctyl ester (as shown in formula (S)-10) S 10 R The method shown in Figure 12 has a synthetic route as shown in the following reaction formula: ; In this fourth embodiment, (2S,10R)-2,10-dimethyldodecyloxytert-butyldiphenylsilane (as shown in formula (S)-10) was synthesized using (S)-p-toluenesulfonic acid 8-tert-butyldiphenylsilyloxy-7-methyloctyl ester (as shown in formula (S)-10). S 10 R The method for synthesizing (2S,10R)-2,10-dimethyldodecyloxytert-butyldiphenylsilane described in Example 4 differs from the method for synthesizing (2S,10S)-2,10-dimethyldodecyloxytert-butyldiphenylsilane described in Example 3 only in that (R)-1-bromo-2-methylbutane (as shown in formula (R)-11) is used instead of (S)-1-bromo-2-methylbutane (as shown in formula (R)-11) in step 1) of Example 4. Example 4 yielded a colorless oily substance (2S,10R)-2,10-dimethyldodecyloxytert-butyldiphenylsilane (881 mg, 91% yield); the structural formula of (2S,10R)-2,10-dimethyldodecyloxytert-butyldiphenylsilane is shown in formula (2S,10R)-12. Specific rotation, 1H NMR, 1C NMR, and high-resolution mass spectrometry were performed on (2S,10R)-2,10-dimethyldodecyloxytert-butyldiphenylsilane. The results are as follows: [α]D 25 = − 3.07 (c 1.69, CHCl3); 1 H NMR (500MHz, CDCl3) δ 7.67 (dt, J = 6.6, 1.6 Hz, 4H), 7.43 – 7.36 (m, 6H), 3.52 –3.49 (m, 1H), 3.43 (dd, J = 9.8, 6.4 Hz, 1H), 1.64 (q, J = 6.5 Hz, 1H), 1.42(ddd, J = 13.1, 6.7, 2.6 Hz, 1H), 1.27 (dt, J = 19.2, 5.6 Hz, 14H), 1.16 –1.09 (m, 2H), 1.06 (s, 9H), 0.92 (d, J = 6.7 Hz, 3H), 0.88 – 0.83 (m, 6H); 13 CNMR (125 MHz, CDCl3) δ 135.78, 134.31, 129.59, 127.68, 69.10, 36.79, 35.85,34.55, 33.29, 30.17, 30.11, 29.85, 29.65, 27.27, 27.11, 27.02, 19.47, 19.38,17.06, 11.57; HRMS (ESI, m / z): calculated for C 30 H 48 OSiNa + [M + Na] + : 475.3377, found: 475.3380; Example 5: A method for synthesizing (2R,10S)-2,10-dimethyldodecyloxytert-butyldiphenylsilane (as shown in formula (R)-10) using (R)-p-toluenesulfonic acid 8-tert-butyldiphenylsilyloxy-7-methyloctyl ester (as shown in formula (R)-10) R 10 S The method shown in Figure 12 has a synthetic route as shown in the following reaction formula: ; In this fifth example, (2R,10S)-2,10-dimethyldodecyloxy-tert-butyldiphenylsilane is synthesized using (R)-p-toluenesulfonic acid 8-tert-butyldiphenylsilyloxy-7-methyloctyl ester (as shown in formula (R)-10). The method for synthesizing (2R,10S)-2,10-dimethyldodecyloxy-tert-butyldiphenylsilane in Example 5 differs from the method for synthesizing (2S,10S)-2,10-dimethyldodecyloxy-tert-butyldiphenylsilane in Example 3 only in that (R)-p-toluenesulfonic acid 8-tert-butyldiphenylsilyloxy-7-methyloctyl ester is used instead of (S)-p-toluenesulfonic acid 8-tert-butyldiphenylsilyloxy-7-methyloctyl ester in step 2) of Example 3. Example 5 yielded a colorless oily substance (2R,10S)-2,10-dimethyldodecyloxytert-butyldiphenylsilane (882 mg, 91% yield); wherein the structural formula of (2R,10S)-2,10-dimethyldodecyloxytert-butyldiphenylsilane is as shown in formula (2R,10S)-12. Specific rotation, 1H NMR, 1C NMR, and high-resolution mass spectrometry were performed on (2R,10S)-2,10-dimethyldodecyloxytert-butyldiphenylsilane. The results are as follows: [α] D 25 = + 9.97 (c 2.65, CHCl3); 1 H NMR (500MHz, CDCl3) δ 7.69 (dt, J = 6.5, 1.7 Hz, 4H), 7.47 – 7.34 (m, 6H), 3.53 (dd,J = 9.7, 5.7 Hz, 1H), 3.45 (dd, J = 9.8, 6.4 Hz, 1H), 1.68 – 1.63 (m, 1H), 1.46 – 1.40 (m, 1H), 1.37 – 1.10 (m, 16H), 1.07 (s, 9H), 0.93 (d, J = 6.7 Hz, 3H), 0.90 – 0.84 (m, 6H); 13C NMR (125 MHz, CDCl3) δ 135.79, 134.35, 134.34,129.60, 127.69, 69.13, 36.81, 35.88, 34.57, 33.32, 30.19, 30.12, 29.86,29.67, 27.29, 27.13, 27.05, 19.49, 19.40, 17.08, 11.58; HRMS (ESI, m / z):calculated for C 30 H 49 OSi + [M + H] + : 452.3481, found: 452.3484; Example 6: A method for synthesizing (2R,10R)-2,10-dimethyldodecyloxytert-butyldiphenylsilane (as shown in formula (R)-10) using (R)-p-toluenesulfonic acid 8-tert-butyldiphenylsilyloxy-7-methyloctyl ester (as shown in formula (R)-10) R 10 R The method shown in Figure 12 has a synthetic route as shown in the following reaction formula: .

[0034] In this embodiment, the method for synthesizing (2R,10R)-2,10-dimethyldodecyloxytert-butyldiphenylsilane using (R)-p-toluenesulfonic acid 8-tert-butyldiphenylsilyloxy-7-methyloctyl ester (as shown in formula (R)-10) is compared with the method for synthesizing (2R,10R)-2,10-dimethyldodecyloxytert-butyldiphenylsilane in Example 5, except that in step 1) of Example 6, (R)-1-bromo-2-methylbutane (as shown in formula (R)-11) is used instead of (S)-1-bromo-2-methylbutane (as shown in formula (R)-11). Example 6 yielded a colorless oily substance (2R,10R)-2,10-dimethyldodecyloxytert-butyldiphenylsilane (901 mg, 93% yield); wherein the structural formula of (2R,10R)-2,10-dimethyldodecyloxytert-butyldiphenylsilane is as shown in formula (2R,10R)-12. Specific rotation, proton NMR, carbon NMR, and high-resolution mass spectrometry were performed on (2R,10R)-2,10-dimethyldodecyloxytert-butyldiphenylsilane. The results are as follows: [α] D25 = − 5.69 (c 0.91, CHCl3); 1 H NMR (500MHz, CDCl3) δ 7.68 (dt, J = 6.8, 1.6 Hz, 4H), 7.45 – 7.36 (m, 6H), 3.52 (dd,J = 9.8, 5.7 Hz, 1H), 3.44 (dd, J = 9.8, 6.4 Hz, 1H), 1.65 (dt, J = 13.2, 6.4Hz, 1H), 1.47 – 1.37 (m, 3H), 1.34 – 1.19 (m, 14H), 1.06 (s, 9H), 0.92 (d, J= 6.7 Hz, 3H), 0.88 – 0.84 (m, 6H); 13 C NMR (126 MHz, CDCl3) δ 135.77, 134.30,129.59, 127.68, 76.91, 69.10, 36.79, 35.84, 34.54, 33.28, 30.17, 30.10,29.84, 29.64, 27.27, 27.10, 27.02, 19.46, 19.37, 17.05, 11.56; HRMS (ESI, m / z): calculated for C 30 H 49 OSi + [M + H] + : 453.3481, found: 453.3483.

[0035] Example 7: A method for synthesizing (3S,11S)-3,11-dimethyl-2,10-dodecyloxy-tert-butyl-diphenylsilane (as shown in formula (2S,10S)-12) (3S,11S)-3,11-dimethyl-2,9-octadecan-12-ene (as shown in formula (3S,11S)-14) using (2S,10S)-2,10-dimethyl-1,9-octadecan-12-ene (3S,11S)-14) via the following reaction route: ; In this seventh example, the method for synthesizing (3S,11S)-3,11-dimethylnonadecano-12-ene (as shown in formula (2S,10S)-12) using (2S,10S)-2,10-dimethyldodecyloxytert-butyldiphenylsilane (as shown in formula (2S,10S)-12) includes the following steps: Step A: Under argon protection and at 0°C, a tetrahydrofuran solution of (2S,10S)-2,10-dimethyldodecyloxytert-butyldiphenylsilane was added to a 20 mL Shrek tube; after thorough stirring, 1.6 mL of a tetrahydrofuran solution of tetrabutylamine fluoride (TBAF) was slowly added; then the temperature was raised to room temperature and stirred overnight; then the reaction was quenched with water (5 mL) to obtain the material; in this application, the tetrahydrofuran solution of (2S,10S)-2,10-dimethyldodecyloxytert-butyldiphenylsilane was obtained by mixing (2S,10S)-2,10-dimethyldodecyloxytert-butyldiphenylsilane (360.0 mg, 0.80 mmol) and tetrahydrofuran (5 mL) evenly, and the molar concentration of tetrabutylamine fluoride (TBAF) in the tetrahydrofuran solution was 1 mol / L; The organic and aqueous phases of the material were then separated. The aqueous phase was extracted three times with ethyl acetate (EtOAc), with 8 mL of ethyl acetate (EtOAc) used in each extraction. The organic phases obtained from the three extractions were then combined with the separated organic phases. The combined organic phases were washed with saturated NaCl solution (10 mL), dried with anhydrous Na2SO4, and then concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel chromatography (petroleum ether / ethyl acetate 5:1) to obtain a colorless oily substance (2S,10S)-2,10-dimethyldodecyl-1-ol (150.0 mg, 88% yield); wherein, the structural formula of (2S,10S)-2,10-dimethyldodecyl-1-ol is shown in formula (2S,10S)-13. Specific rotation, 1H NMR, 1C NMR, and high-resolution mass spectrometry were performed on (2S,10S)-2,10-dimethyldodecyl-1-ol. The results are as follows: [α] D 25 = + 0.26 (c 1.51, CHCl3); 1 H NMR (500 MHz, CDCl3) δ 3.44(dd, J = 10.5, 5.7 Hz, 1H), 3.35 (dd, J = 10.5, 6.5 Hz, 1H), 1.54 (dq, J =12.7, 6.6 Hz, 1H), 1.37 (s, 1H), 1.32 – 1.13 (m, 14H), 1.03 (dt, J = 16.8,7.4 Hz, 3H), 0.85 (d, J = 6.7 Hz, 3H), 0.81 – 0.75 (m, 6H); 13C NMR (126 MHz, CDCl3) δ 68.59, 36.78, 35.92, 34.55, 33.31, 30.16, 30.11, 29.84, 29.65,27.25, 27.14, 19.37, 16.73, 11.55; HRMS (ESI, m / z): calculated for C 14 H 31 O + [M +H] + : 214.2305, found: 214.2309; Step B: Under argon protection and at 0°C, add (2S,10S)-2,10-dimethyldodecyl-1-ol (150.0 mg, 0.70 mmol) and dichloromethane (DCM) (10 mL) to a 50 mL single-necked flask; after thorough stirring, add DMP reagent (445.0 mg, 1.05 mmol). The DMP reagent is added in batches, specifically in four batches of 111.25 mg each; then heat to room temperature and stir continuously for 2 hours to obtain a reaction solution; filter the reaction solution, and then concentrate the filtrate under reduced pressure to obtain crude product I; At -35°C, 611.0 mg (1.05 mmol) of heptadecanyl bromotriphenylphosphine and 10 mL of tetrahydrofuran (THF) were added to a 50 mL Shrek tube. The structural formula of heptadecanyl bromotriphenylphosphine is [insert structural formula here]. In this application, bromo(heptadecyl)triphenylphosphine was synthesized using the method disclosed in the paper "Synthesis ofracemic and each enantiomer of 3-methylnonacosanol, a new plant growth regulator from Lowsonia inermis". After thorough stirring and dissolution, 0.44 mL of n-BuLi in n-hexane solution was slowly added dropwise, with a molar concentration of n-BuLi of 2.4 mol / L. The temperature was then raised to room temperature and stirred continuously for 0.5 h, followed by cooling to -35 °C to obtain the reaction system. Crude product I was then dissolved in tetrahydrofuran (THF) (3 mL) and added dropwise to the reaction system. The temperature was then raised to room temperature and stirred continuously overnight. Finally, the reaction was quenched using saturated NH4Cl solution (8 mL). After quenching the reaction, the organic phase and the aqueous phase were separated. The aqueous phase was extracted three times with ethyl acetate (EtOAc), with 10 mL of ethyl acetate (EtOAc) used in each extraction. The organic phases obtained from the three extractions were then combined with the organic phases separated in this step. The combined organic phases were washed with saturated NaCl solution (15 mL), dried with anhydrous Na2SO4, and then concentrated under reduced pressure to obtain crude product II. The crude product II was purified by silica gel chromatography (petroleum ether) to obtain a white waxy solid (3S,11S)-3,11-dimethylnonadecano-12-ene (207.0 mg, 68% yield); wherein the structural formula of (3S,11S)-3,11-dimethylnonadecano-12-ene is shown in formula (3S,11S)-14.

[0036] Specific rotation, 1H NMR, 1C NMR, and high-resolution mass spectrometry were performed on (3S,11S)-3,11-dimethyl-9-neocode-12-ene. The results are as follows: [α] D 25 = + 1.46 (c 0.55, CHCl3); 1 H NMR (500 MHz, CDCl3)δ 5.36 – 4.94 (m, 2H), 1.96 – 1.88 (m, 3H), 1.61 – 1.44 (m, 2H), 1.19 (s,43H), 0.85 – 0.75 (m, 12H); 13 C NMR (126 MHz, CDCl3) δ 136.58, 130.06, 128.51,37.76, 36.81, 34.57, 32.09, 31.78, 30.20, 30.11, 30.01, 29.93, 29.90, HRMS (ESI, m / z): calculated for C 31 H 63 + [M + H] + :435.4860, found: 435.4863.

[0037] Example 8: A method for synthesizing (3R,11S)-3,11-dimethyl-2,10-dodecyloxy-tert-butyl-2-phenylsilane (as shown in formula (2S,10R)-12) (3R,11S)-3,11-dimethyl-2,9-neco-12-ene (as shown in formula (3R,11S)-14) using (2S,10R)-2,10-dimethyl-2,10-dodecyloxy-tert-butyl-2-phenylsilane (as shown in formula (2S,10R)-12) is provided, and the synthetic route is shown in the following reaction formula: ; In this application, step A of the method for synthesizing (3R,11S)-3,11-dimethylnonadecano-12-ene (as in formula (3R,11S)-14) in Example 8 differs from step A of the method for synthesizing (3S,11S)-3,11-dimethylnonadecano-12-ene (as in formula (3S,11S)-14) in Example 7 in that: In step A of the method described in Example 8, (2S,10R)-2,10-dimethyldodecyloxytert-butyldiphenylsilane (203.0 mg, 0.45 mmol) with the structural formula (2S,10R)-12 was used instead of (2S,10S)-2,10-dimethyldodecyloxytert-butyldiphenylsilane (360.0 mg, 0.80 mmol) used in step A of the method described in Example 7; the amount of tetrabutylammonium fluoride (TBAF) tetrahydrofuran solution added in step A of the method described in Example 8 was 0.9 mL.

[0038] In Example 8, step A yielded a colorless oily substance (2S,10R)-2,10-dimethyldodecyl-1-ol (88.0 mg, 91% yield); the structural formula of (2S,10R)-2,10-dimethyldodecyl-1-ol is shown in formula (2S,10R)-13.

[0039] Specific rotation, 1H NMR, 1C NMR, and high-resolution mass spectrometry were performed on (2S,10R)-2,10-dimethyldodecyl-1-ol. The results are as follows: [α] D 25 = − 0.67 (c 2.39, CHCl3); 1 H NMR (500 MHz, CDCl3) δ 3.44(dd, J = 10.5, 5.7 Hz, 1H), 3.35 (dd, J = 10.5, 6.5 Hz, 1H), 1.58 – 1.51 (m,1H), 1.48 – 1.38 (m, 1H), 1.33 – 1.15 (m, 14H), 1.08 – 0.99 (m, 3H), 0.85 (d,J = 6.7 Hz, 3H), 0.81 – 0.75 (m, 6H); 13HRMS (ESI, m / z): calculated for C 14 H 31 O + [M + H] + : 214.2305, found:214.2311; In this application, the difference between step B in the method for synthesizing (3R,11S)-3,11-dimethylnonadecano-12-ene (as in formula (3R,11S)-14) in Example 8 and step B in the method for synthesizing (3S,11S)-3,11-dimethylnonadecano-12-ene in Example 7 is as follows: In step B of the method described in Example 8, (2S,10R)-2,10-dimethyldodecyl-1-ol (173.0 mg, 0.81 mmol) with the structural formula (2S,10R)-13 was used instead of (2S,10S)-2,10-dimethyldodecyl-1-ol (150.0 mg, 0.70 mmol); in step B of the method described in Example 8, the amount of DMP reagent added was 517.0 mg, the amount of bromo(heptadecyl)triphenylphosphine added was 710.0 mg, and the amount of n-BuLi n-hexane solution added was 0.51 mL; Step B of Example 8 yielded a white waxy solid (3R,11S)-3,11-dimethylnonadecano-12-ene (222.0 mg, 63% yield); wherein the structural formula of (3R,11S)-3,11-dimethylnonadecano-12-ene is shown in Formula (3R,11S)-14. Specific rotation, 1H NMR, 1C NMR, and high-resolution mass spectrometry were performed on (3R,11S)-3,11-dimethyl-9-neco-12-ene. The results are as follows: [α] D 25 = − 0.71 (c 2.31, CHCl3); 1 H NMR (500 MHz, CDCl3)δ 5.34 – 4.99 (m, 2H), 1.92 (m, 3H), 1.65 – 1.36 (m, 2H), 1.19 (s, 46H), 0.87– 0.72 (m, 12H); 13C NMR (126 MHz, CDCl3) δ 136.58, 130.53, 130.06, 128.51,37.76, 36.81, 34.57, 32.77, 32.09, 31.78, 30.20, 30.11, 30.01, 29.94, 29.90,29.86, 29.82, 29.73, 29.69, 29.66, 29.52, 29.48, 29.33, 27.69, 27.65, 27.37,27.28, 22.85, 21.59, 19.38, 14.27, 11.56; HRMS (ESI, m / z): calculated for C 31 H 63 + [M + H] + : 435.4859, found: 435.4858.

[0040] Example 9: A method for synthesizing (3S,11R)-3,11-dimethyl-2,10-dodecyloxy-tert-butyl-2-phenylsilane (as shown in formula (2R,10S)-12) (3S,11R)-3,11-dimethyl-2,9-octadecan-12-ene (as shown in formula (3S,11R)-14) using (2R,10S)-2,10-dimethyl-2,10-dodecyloxy-tert-butyl-2-phenylsilane (as shown in formula (2R,10S)-12) is provided, and the synthetic route is shown in the following reaction formula: ; In this application, the difference between step A of the method for synthesizing (3S,11R)-3,11-dimethylnonadecano-12-ene in Example 9 and step A of the method for synthesizing (3S,11S)-3,11-dimethylnonadecano-12-ene (as in formula (3S,11S)-14) in Example 7 is as follows: In step A of the method described in Example 9, (2R,10S)-2,10-dimethyldodecyloxytert-butyldiphenylsilane (332.0 mg, 0.73 mmol) with the structural formula (2R,10S)-12 was used instead of (2S,10S)-2,10-dimethyldodecyloxytert-butyldiphenylsilane (360.0 mg, 0.80 mmol) used in step A of the method described in Example 7; the amount of tetrabutylammonium fluoride (TBAF) tetrahydrofuran solution added in step A of the method described in Example 9 was 1.46 mL.

[0041] In Example 9, step A yielded a colorless oily substance (2R,10S)-2,10-dimethyldodecyl-1-ol (140.0 mg, 89% yield); the structural formula of (2R,10S)-2,10-dimethyldodecyl-1-ol is shown in formula (2R,10S)-13.

[0042] Specific rotation, 1H NMR, 1C NMR, and high-resolution mass spectrometry were performed on (2R,10S)-2,10-dimethyldodecyl-1-ol. The results are as follows: [α] D 25 = + 13.03 (c 1.01, CHCl3); 1 H NMR (500 MHz, CDCl3) δ3.33 (dd, J = 10.5, 5.7 Hz, 1H), 3.24 (dd, J = 10.5, 6.5 Hz, 1H), 1.46 – 1.38(m, 1H), 1.20 – 1.04 (m, 15H), 0.97 – 0.87 (m, 3H), 0.73 (d, J = 6.7 Hz, 3H), 0.69 – 0.64 (m, 6H); 13 C NMR (126 MHz, CDCl3) δ 69.60, 37.78, 36.92, 35.55,34.30, 31.16, 31.11, 30.84, 30.65, 28.25, 28.14, 20.37, 17.73, 12.55; HRMS(ESI, m / z): calculated for C 14 H 31 O + [M + H] + : 215.2305, found: 215.2300.

[0043] In this application, the difference between step B in the method described in Embodiment 9 and step B in the method described in Embodiment 7 is as follows: In step B of the method described in Example 9, (2R,10S)-2,10-dimethyldodecyl-1-ol (190.0 mg, 0.89 mmol) with the structural formula (2R,10S)-13 was used instead of (2S,10S)-2,10-dimethyldodecyl-1-ol (150.0 mg, 0.70 mmol); in step B of the method described in Example 9, the amount of DMP reagent added was 568.0 mg, the amount of bromo(heptadecyl)triphenylphosphine added was 779.0 mg, and the amount of n-BuLi n-hexane solution added was 0.56 mL; Step B of Example 9 yielded a white waxy solid (3S,11R)-3,11-dimethylnonadecano-12-ene (as shown in formula (3S,11R)-14) (256.0 mg, 66% yield); wherein the structural formula of (3S,11R)-3,11-dimethylnonadecano-12-ene is shown in formula (3S,11R)-14. Specific rotation, 1H NMR, 1C NMR, and high-resolution mass spectrometry were performed on (3S,11R)-3,11-dimethyl-9-neocode-12-ene. The results are as follows: [α] D 25 = + 1.33 (c 0.81, CHCl3); 1 H NMR (500 MHz, CDCl3)δ 5.34 – 4.96 (m, 2H), 2.00 – 1.84 (m, 3H), 1.71 – 1.38 (m, 2H), 1.19 (s,43H), 0.87 – 0.74 (m, 12H); 13 C NMR (126 MHz, CDCl3) δ 136.58, 130.53, 130.06,128.51, 37.76, 36.81, 34.57, 32.77, 32.09, 31.78, 30.20, 30.11, 30.01, 29.94,29.90, 29.86, 29.82, 29.73, 29.69, 29.66, 29.52, 29.48, 29.33, 27.69, 27.65,27.37, 27.28, 22.85, 21.59, 19.38, 14.27, 11.56; HRMS (ESI, m / z): calculated for C 31 H 63 + [M + H] + : 457.4755, found: 457.4759.

[0044] Example 10: A method for synthesizing (3R,11R)-3,11-dimethyl-2,10-dodecyloxy-tert-butyl-2-phenylsilane (as shown in formula (2R,10R)-12) (3R,11R)-3,11-dimethyl-2,9-octadecan-12-ene (as shown in formula (3R,11R)-14) using (2R,10R)-2,10-dimethyl-2,10-dodecyloxy-tert-butyl-2-phenylsilane (as shown in formula (2R,10R)-12) is provided, and the synthetic route is shown in the following reaction formula: ; In this application, step A of the method for synthesizing (3R,11R)-3,11-dimethylnonadecano-12-ene (as in formula (3R,11R)-14) in Example 10 differs from step A of the method for synthesizing (3S,11S)-3,11-dimethylnonadecano-12-ene (as in formula (3S,11S)-14) in Example 7 in that: In step A of the method described in Example 10, (2R,10R)-2,10-dimethyldodecyloxytert-butyldiphenylsilane (210.0 mg, 0.46 mmol) with the structural formula (2R,10R)-12 was used instead of (2S,10S)-2,10-dimethyldodecyloxytert-butyldiphenylsilane (360.0 mg, 0.80 mmol) used in step A of the method described in Example 7; the amount of tetrabutylammonium fluoride (TBAF) tetrahydrofuran solution added in step A of the method described in Example 10 was 0.93 mL.

[0045] The method step A described in Example 10 yielded a colorless oily substance (2R,10R)-2,10-dimethyldodecyl-1-ol (126.0 mg, 80% yield); wherein the structural formula of (2R,10R)-2,10-dimethyldodecyl-1-ol is as shown in formula (2R,10R)-13.

[0046] Specific rotation, 1H NMR, 1C NMR, and high-resolution mass spectrometry were performed on (2R,10R)-2,10-dimethyldodecyl-1-ol. The results are as follows: [α] D 25 = − 10.56 (c 0.95, CHCl3); 1 H NMR (500 MHz, CDCl3) δ3.44 (dd, J = 10.5, 5.8 Hz, 1H), 3.35 (dd, J = 10.5, 6.6 Hz, 1H), 1.57 – 1.50(m, 2H), 1.29 – 1.14 (m, 15H), 1.06 – 1.01 (m, 2H), 0.85 (d, J = 6.7 Hz, 3H), 0.80 – 0.76 (m, 6H); 13 C NMR (126 MHz, CDCl3) δ 69.59, 37.78, 36.92, 35.55,34.30, 31.16, 31.11, 30.84, 30.65, 28.25, 28.14, 20.37, 17.73, 12.55; HRMS(ESI, m / z): calculated for C 14 H 31O + [M + H] + : 215.2305, found: 215.2304.

[0047] In this application, the difference between step B in the method for synthesizing (3R,11R)-3,11-dimethylnonadecano-12-ene as shown in Example 10 and step B in the method for synthesizing (3S,11S)-3,11-dimethylnonadecano-12-ene in Example 7 is as follows: In step B of the method described in Example 10, (2R,10R)-2,10-dimethyldodecyl-1-ol (106.0 mg, 0.50 mmol) with the structural formula (2R,10R)-13 was used instead of (2S,10S)-2,10-dimethyldodecyl-1-ol (150.0 mg, 0.70 mmol) in step B of the method described in Example 7; in step B of the method described in Example 10, the amount of DMP reagent added was 318.0 mg, the amount of bromo(heptadecyl)triphenylphosphine added was 436.0 mg, and the amount of n-BuLi n-hexane solution added was 0.32 mL; Step B of the method described in Example 10 yielded a white waxy solid (3R,11R)-3,11-dimethylnonadecano-12-ene (154.0 mg, 71% yield); wherein (3R,11R)-3,11-dimethylnonadecano-12-ene is as shown in formula (3R,11R)-14.

[0048] Specific rotation, 1H NMR, 1C NMR, and high-resolution mass spectrometry were performed on (3R,11R)-3,11-dimethyl-9-neco-12-ene. The results are as follows: [α] D 25 = -3.61 (c 0.95, CHCl3); 1 H NMR (500 MHz, CDCl3)δ 5.41 – 5.09 (m, 2H), 2.11 – 1.94 (m, 3H), 1.57 (s, 2H), 1.28 (s, 43H), 0.95– 0.84 (m, 12H); 13C NMR (126 MHz, CDCl3) δ 136.58, 130.06, 128.51, 37.76,36.81, 34.56, 32.08, 31.77, 30.20, 30.10, 30.00, 29.93, 29.90, 29.86, HRMS (ESI, m / z): calculated for C 31 H 63 + [M + H] + : 435.4860, found: 435.4866.

[0049] Example 11: 3,11-Dimethylnonacosane is a major component of the aggregation pheromone of the German cockroach; in Example 11 of this application, a method for synthesizing (3S,11R)-3,11-dimethylnonacosane (as shown in formula (3S,11R)-1) using (3S,11S)-3,11-dimethylnonacosane-12-ene (as shown in formula (3S,11S)-14) is described in the following reaction formula: ; In this eleventh example, the method for synthesizing (3S,11R)-3,11-dimethylnonadec-12-ene includes the following steps: Under hydrogen protection and at room temperature, 13.0 mg of palladium on carbon (Pd / C) catalyst was added to a 50 mL Shrek tube, where the mass of palladium in the Pd / C catalyst accounted for 10% of the total mass of the Pd / C catalyst. The tube was then evacuated and the gas inside was replaced with hydrogen using a hydrogen balloon. Methanol (MeOH) (5 mL) was then added, and after thorough stirring, (3S,11S)-3,11-dimethylnonadecano-12-ene (130.0 mg, 0.30 mmol) was slowly added. The mixture was then stirred overnight under hydrogen conditions. The mixture was then filtered through diatomaceous earth, and the filtrate was concentrated under reduced pressure to obtain a crude product. The crude product was purified by silica gel chromatography (petroleum ether) to obtain a white waxy solid (3S,11R)-3,11-dimethylnonadecanoane (162.0 mg, 97% yield). The structural formula of (3S,11R)-3,11-dimethylnonadecanoane is shown in formula (3S,11R)-1. Specific rotation, 1H NMR, 1C NMR, and high-resolution mass spectrometry were performed on (3S,11R)-3,11-dimethylnonacosane. The results are as follows: [α] D 25 = + 3.59 (c 0.78, CHCl3); 1 H NMR (500 MHz, CDCl3) δ 1.40– 1.08 (m, 48H), 1.06 – 0.91 (m, 4H), 0.83 – 0.75 (m, 12H); 13 C NMR (126 MHz, CDCl3) δ 36.09, 35.65, 33.40, 31.74, 30.92, 29.04, 28.77, 28.73, 28.69,28.65, 28.49, 28.36, 26.11, 26.08, 21.68, 18.71, 18.21, 13.10, 10.39; HRMS(ESI, m / z): calculated for C 31 H 65 + [M + H] + : 437.5015, found: 437.5019.

[0050] Example 12: A method for synthesizing (3R,11R)-3,11-dimethylnonadecane (as shown in formula (3R,11R)-1 from (3R,11S)-3,11-dimethylnonadecane (as shown in formula (3R,11S)-14) is provided, and the synthetic route is shown in the following reaction formula: ; The method for synthesizing (3R,11R)-3,11-dimethylnonacontane in Example XII differs from the method for synthesizing (3S,11R)-3,11-dimethylnonacontane in Example XXI in that: The method described in Example 12 uses (3R,11S)-3,11-dimethylnonadecano-12-ene (170.0 mg, 0.39 mmol) as shown in Formula (3R,11S)-14 instead of (3S,11S)-3,11-dimethylnonadecano-12-ene (130.0 mg, 0.30 mmol) used in the method described in Example 11; in the method described in Example 12, the amount of palladium on carbon catalyst used is 17.0 mg.

[0051] The method described in Example 12 yielded a white waxy solid (3R,11R)-3,11-dimethylnonacosane (165.0 mg, 97% yield); wherein the structural formula of (3R,11R)-3,11-dimethylnonacosane is shown in Formula (3R,11R)-1.

[0052] Specific rotation, 1H NMR, 1C NMR, and high-resolution mass spectrometry were performed on (3R,11R)-3,11-dimethylnonacosane. The results are as follows: [α] D 25 = − 0.53 (c 1.69, CHCl3); 1 H NMR (500 MHz, CDCl3) δ 1.19(s, 48H), 1.08 – 0.96 (m, 4H), 0.85 – 0.74 (m, 12H); 13 C NMR (126 MHz, CDCl3) δ37.25, 36.81, 34.56, 32.91, 32.08, 30.20, 29.93, 29.89, 29.86, 29.82, 29.66,29.52, 27.28, 27.25, 22.85, 19.88, 19.38, 14.27, 11.56; HRMS (ESI, m / z):calculated for C 31 H 65 + [M + H] + : 437.5016, found: 437.5021; Example 13: A method for synthesizing (3S,11S)-3,11-dimethylnonadecane (as shown in formula (3S,11S)-1 from (3S,11R)-3,11-dimethylnonadecane (as shown in formula (3S,11R)-14) is provided, and the synthetic route is shown in the following reaction formula: ; The method for synthesizing (3S,11S)-3,11-dimethylnonacontane in Example Thirteen differs from the method for synthesizing (3S,11S)-3,11-dimethylnonacontane in Example Eleven in that: The method described in Example 13 uses (3S,11R)-3,11-dimethylnonadecano-12-ene (157.0 mg, 0.36 mmol) as shown in Formula (3S,11R)-14 instead of (3S,11S)-3,11-dimethylnonadecano-12-ene (130.0 mg, 0.30 mmol) used in the method described in Example 11; in the method described in Example 13, the amount of palladium on carbon catalyst used is 16.0 mg.

[0053] The method described in Example 13 yielded a white waxy solid (3S,11S)-3,11-dimethylnonacosane (150.0 mg, 95% yield); wherein the structural formula of (3S,11S)-3,11-dimethylnonacosane is shown in Formula (3S,11S)-1.

[0054] Specific rotation, 1H NMR, 1C NMR, and high-resolution mass spectrometry were performed on (3S,11S)-3,11-dimethylnonacosane. The results are as follows: [α] D 25 = + 1.47 (c 0.93, CHCl3); 1 H NMR (500 MHz, CDCl3) δ 1.19(s, 48H), 1.07 – 0.95 (m, 4H), 0.83 – 0.75 (m, 12H); 13 C NMR (126 MHz, CDCl3) δ37.26, 36.82, 34.57, 32.92, 32.09, 30.21, 29.94, 29.90, 29.87, 29.83, 29.67,29.53, 27.29, 27.26, 22.86, 19.89, 19.39, 14.28, 11.57; HRMS (ESI, m / z):calculated for C 31 H 65 + [M + H] + : 437.5015, found: 437.5021; Example 14: A method for synthesizing (3R,11S)-3,11-dimethylnonadecane (as shown in formula (3R,11S)-1 from (3R,11R)-3,11-dimethylnonadecane (as shown in formula (3R,11R)-14) is provided, and the synthetic route is shown in the following reaction formula: ; In this embodiment, the method for synthesizing (3R,11S)-3,11-dimethylnonadecane using (3R,11R)-3,11-dimethylnonadecane includes the following steps: The method for synthesizing (3R,11S)-3,11-dimethylnonacontane in Example Fourteen differs from the method for synthesizing (3S,11S)-3,11-dimethylnonacontane in Example Eleven in that: The method described in Example 14 uses (3R,11R)-3,11-dimethylnonadecano-12-ene (110.0 mg, 0.25 mmol) as shown in Formula (3R,11R)-14 to replace (3S,11S)-3,11-dimethylnonadecano-12-ene (130.0 mg, 0.30 mmol) used in the method described in Example 11; in the method described in Example 14, the amount of palladium on carbon catalyst used is 11.0 mg.

[0055] The method described in Example 14 yielded (3R,11S)-3,11-dimethylnonacosane (as shown in Formula (3R,11S)-1) (104.0 mg, 94% yield); wherein the structural formula of (3R,11S)-3,11-dimethylnonacosane is shown in Formula (3R,11S)-1.

[0056] Specific rotation, 1H NMR, 1C NMR, and high-resolution mass spectrometry were performed on (3R,11S)-3,11-dimethylnonacosane. The results are as follows: [α] D 25 = -4.41 (c 1.26, CHCl3); 1 H NMR (500 MHz, CDCl3) δ 1.54– 1.46 (m, 2H), 1.19 (s, 50H), 0.83 – 0.77 (m, 12H); 13 C NMR (126 MHz, CDCl3) δ37.26, 36.82, 34.57, 32.91, 32.09, 30.21, 29.94, 29.90, 29.87, 29.83, 29.66,29.53, 27.29, 27.25, 22.86, 19.89, 19.39, 14.28, 11.57; HRMS (ESI, m / z):calculated for C 31 H 65 + [M + H] + : 437.5015, found: 437.5014.

[0057] Example 15: A method for synthesizing (3S,11R)-3,11-dimethylnonacosane (as shown in formula (3S,11R)-1) includes the following steps: First, using (S)-p-toluenesulfonic acid 8-tert-butyldiphenylsilyloxy-7-methyloctyl ester (as shown in formula (S)-10) as a starting material, (2S,10S)-2,10-dimethyldodecyloxytert-butyldiphenylsilane (as shown in formula (2S,10S)-12) was synthesized; wherein, the synthesis method of (S)-p-toluenesulfonic acid 8-tert-butyldiphenylsilyloxy-7-methyloctyl ester in Example 15 was consistent with the synthesis method of (S)-p-toluenesulfonic acid 8-tert-butyldiphenylsilyloxy-7-methyloctyl ester described in Example 1; the synthesis method of (2S,10S)-2,10-dimethyldodecyloxytert-butyldiphenylsilane in Example 15 was consistent with the synthesis method of (2S,10S)-2,10-dimethyldodecyloxytert-butyldiphenylsilane described in Example 3. Then, using (2S,10S)-2,10-dimethyldodecyloxytert-butyldiphenylsilane (as shown in formula (2S,10S)-12) as a raw material, (3S,11S)-3,11-dimethylnonadecano-12-ene (as shown in formula (3S,11S)-14) was synthesized; the method for synthesizing (3S,11S)-3,11-dimethylnonadecano-12-ene in Example 15 was consistent with the method for synthesizing (3S,11S)-3,11-dimethylnonadecano-12-ene described in Example 7. Finally, using (3S,11S)-3,11-dimethylnonadecane-12-ene (as shown in formula (3S,11S)-14) as a starting material, (3S,11R)-3,11-dimethylnonadecane (as shown in formula (3S,11R)-1) was synthesized; the method for synthesizing (3S,11R)-3,11-dimethylnonadecane in Example 15 is consistent with the method for synthesizing (3S,11R)-3,11-dimethylnonadecane described in Example 11.

[0058] Example 16: A method for synthesizing (3R,11R)-3,11-dimethylnonacosane (as shown in formula (3R,11R)-1) includes the following steps: First, using (S)-p-toluenesulfonic acid 8-tert-butyldiphenylsilyloxy-7-methyloctyl ester (as shown in formula (S)-10) as a starting material, (2S,10R)-2,10-dimethyldodecyloxytert-butyldiphenylsilane (as shown in formula (2S,10R)-12) was synthesized; wherein, the synthesis method of (S)-p-toluenesulfonic acid 8-tert-butyldiphenylsilyloxy-7-methyloctyl ester in Example Sixteen was consistent with the synthesis method of (S)-p-toluenesulfonic acid 8-tert-butyldiphenylsilyloxy-7-methyloctyl ester described in Example One; the synthesis method of (2S,10R)-2,10-dimethyldodecyloxytert-butyldiphenylsilane in Example Sixteen was consistent with the synthesis method of (2S,10R)-2,10-dimethyldodecyloxytert-butyldiphenylsilane described in Example Four. Then, using (2S,10R)-2,10-dimethyldodecyloxytert-butyldiphenylsilane (as shown in formula (2S,10R)-12) as a raw material, (3R,11S)-3,11-dimethylnonadecano-12-ene (as shown in formula (3R,11S)-14) was synthesized; the method for synthesizing (3R,11S)-3,11-dimethylnonadecano-12-ene in Example Sixteen is consistent with the method for synthesizing (3R,11S)-3,11-dimethylnonadecano-12-ene described in Example Eight; Finally, using (3R,11S)-3,11-dimethylnonadecane-12-ene (as shown in formula (3R,11S)-14) as a starting material, (3R,11R)-3,11-dimethylnonadecane (as shown in formula (3R,11R)-1) was synthesized; the method for synthesizing (3R,11R)-3,11-dimethylnonadecane in Example Sixteen is consistent with the method for synthesizing (3R,11R)-3,11-dimethylnonadecane described in Example Twelve.

[0059] Example 17: A method for synthesizing (3S,11S)-3,11-dimethylnonacosane (as shown in formula (3S,11S)-1) includes the following steps: First, using (R)-p-toluenesulfonic acid-8-tert-butyldiphenylsilyloxy-7-methyloctyl ester (as shown in formula (R)-10) as a starting material, (2R,10S)-2,10-dimethyldodecyloxy-tert-butyldiphenylsilane (as shown in formula (R)-12) was synthesized; wherein, the method for synthesizing (R)-p-toluenesulfonic acid-8-tert-butyldiphenylsilyloxy-7-methyloctyl ester in Example 17 was consistent with the method for synthesizing (R)-p-toluenesulfonic acid-8-tert-butyldiphenylsilyloxy-7-methyloctyl ester described in Example 2; the method for synthesizing (2R,10S)-2,10-dimethyldodecyloxy-tert-butyldiphenylsilane in Example 17 was consistent with the method for synthesizing (2R,10S)-2,10-dimethyldodecyloxy-tert-butyldiphenylsilane described in Example 5. Then, using (2R,10S)-2,10-dimethyldodecyloxytert-butyldiphenylsilane (as shown in formula (2R,10S)-12) as a raw material, (3S,11R)-3,11-dimethylnonadecano-12-ene (as shown in formula (3S,11R)-14) was synthesized; wherein, the method for synthesizing (3S,11R)-3,11-dimethylnonadecano-12-ene in Example 17 was consistent with the method for synthesizing (3S,11R)-3,11-dimethylnonadecano-12-ene described in Example 9; Finally, using (3S,11R)-3,11-dimethylnonadecane-12-ene (as shown in formula (3S,11R)-14) as a starting material, (3S,11S)-3,11-dimethylnonadecane (as shown in formula (3S,11S)-1) was synthesized; the method for synthesizing (3S,11S)-3,11-dimethylnonadecane in Example 17 is consistent with the method for synthesizing (3S,11S)-3,11-dimethylnonadecane described in Example 13.

[0060] Example 18: A method for synthesizing (3R,11S)-3,11-dimethylnonacosane (as shown in formula (3R,11S)-1) includes the following steps: First, using (R)-p-toluenesulfonic acid-8-tert-butyldiphenylsilyloxy-7-methyloctyl ester (as shown in formula (R)-10) as a starting material, (2R,10R)-2,10-dimethyldodecyloxy-tert-butyldiphenylsilane (as shown in formula (R)-12) was synthesized; wherein, the synthesis method of (R)-p-toluenesulfonic acid-8-tert-butyldiphenylsilyloxy-7-methyloctyl ester in Example 18 was consistent with the synthesis method of (R)-p-toluenesulfonic acid-8-tert-butyldiphenylsilyloxy-7-methyloctyl ester described in Example 2; the synthesis method of (2R,10R)-2,10-dimethyldodecyloxy-tert-butyldiphenylsilane in Example 18 was consistent with the synthesis method of (2R,10R)-2,10-dimethyldodecyloxy-tert-butyldiphenylsilane described in Example 6. Then, using (2R,10R)-2,10-dimethyldodecyloxytert-butyldiphenylsilane (as shown in formula (2R,10R)-12) as a raw material, (3R,11R)-3,11-dimethylnonadecano-12-ene (as shown in formula (3R,11R)-14) was synthesized; in Example 18, the method for synthesizing (3R,11R)-3,11-dimethylnonadecano-12-ene was the same as the method for synthesizing (3R,11R)-3,11-dimethylnonadecano-12-ene described in Example 10; Finally, using (3R,11R)-3,11-dimethylnonadecane-12-ene (as shown in formula (3R,11R)-14) as a starting material, (3R,11S)-3,11-dimethylnonadecane (as shown in formula (3R,11S)-1) was synthesized; the method for synthesizing (3R,11S)-3,11-dimethylnonadecane in Example 18 is consistent with the method for synthesizing (3R,11S)-3,11-dimethylnonadecane described in Example 14.

Claims

1. A p-toluenesulfonic acid 8-tert-butyldiphenylsilyloxy-7-methyloctyl ester, characterized in that: Its structural formula is shown below: 。 2. The p-toluenesulfonic acid 8-tert-butyldiphenylsilyloxy-7-methyloctyl ester according to claim 1, characterized in that: The p-toluenesulfonic acid 8-tert-butyldiphenylsilyloxy-7-methyloctyl ester is in the S configuration, and the structural formula of the S-configured p-toluenesulfonic acid 8-tert-butyldiphenylsilyloxy-7-methyloctyl ester is shown in formula (S)-10: 。 3. The 8-tert-butyldiphenylsilyloxy-7-methyloctyl ester of p-toluenesulfonic acid according to claim 1, characterized in that: The p-toluenesulfonic acid 8-tert-butyldiphenylsilyloxy-7-methyloctyl ester has an R configuration, and the structural formula of the R-configured p-toluenesulfonic acid 8-tert-butyldiphenylsilyloxy-7-methyloctyl ester is shown in formula (R)-10: 。 4. A method for synthesizing p-toluenesulfonic acid-8-tert-butyldiphenylsilyloxy-7-methyloctyl ester, characterized in that: The p-toluenesulfonate-8-tert-butyldiphenylsilyloxy-7-methyloctyl ester is the p-toluenesulfonate-8-tert-butyldiphenylsilyloxy-7-methyloctyl ester according to claim 1, and the method for synthesizing the p-toluenesulfonate-8-tert-butyldiphenylsilyloxy-7-methyloctyl ester includes the following steps: Starting with 8-bromooctanoic acid, it first reacts with t-BuOK and 18-crown ether-6; then reacts with pentanoyl chloride to generate an anhydride, followed by acylation with 4-benzyloxazolidine-2-one; then undergoes diastereoselective methylation; then NaBH4 reduction; then hydroxyl protection using TBDPSCl; then hydroboration oxidation to oxidize the olefin to an alcohol; finally, TsCl sulfonation to synthesize p-toluenesulfonic acid-8-tert-butyldiphenylsilyloxy-7-methyloctyl ester.

5. The method for synthesizing p-toluenesulfonic acid-8-tert-butyldiphenylsilyloxy-7-methyloctyl ester according to claim 4, characterized in that: When 4-benzyloxazolidin-2-one is (S)-4-benzyloxazolidin-2-one, step S7 yields 8-tert-butyldiphenylsilyloxy-7-methyloctyl p-toluenesulfonic acid in the S configuration.

6. The method for synthesizing p-toluenesulfonic acid-8-tert-butyldiphenylsilyloxy-7-methyloctyl ester according to claim 4, characterized in that: When 4-benzyloxazolidin-2-one is (R)-4-benzyloxazolidin-2-one, step S7 yields 8-tert-butyldiphenylsilyloxy-7-methyloctyl ester of p-toluenesulfonic acid with the R configuration.

7. A method for synthesizing 2,10-dimethyldodecyloxytert-butyldiphenylsilane based on 8-tert-butyldiphenylsilyloxy-7-methyloctyl ester of p-toluenesulfonate, characterized in that: The p-toluenesulfonate-8-tert-butyldiphenylsilyloxy-7-methyloctyl ester is the p-toluenesulfonate-8-tert-butyldiphenylsilyloxy-7-methyloctyl ester according to claim 1; the method for synthesizing 2,10-dimethyldodecyloxytert-butyldiphenylsilane includes the following steps: 2,10-Dimethyldodecyloxytert-butylsilylsilyl-7-methyloctyl ester of p-toluenesulfonic acid was prepared by nucleophilic substitution reaction with Grignard reagent, which was made from bromide and Mg.

8. A method for synthesizing 3,11-dimethyl-2,9-dicarbon-12-ene based on 2,10-dimethyldodecyloxy-tert-butyldiphenylsilane, characterized in that: The 2,10-dimethyldodecyloxytert-butyldiphenylsilane is the 2,10-dimethyldodecyloxytert-butyldiphenylsilane according to claim 7; the method for synthesizing the 3,11-dimethylnonadecano-12-ene includes the following steps: A. 2,10-Dimethyldodecyloxytert-butyldiphenylsilane was deprotected with TBAF to obtain 2,10-dimethyldodecyl-1-ol; B. The hydroxyl group of 2,10-dimethyldodecyl-1-ol was converted to an aldehyde group by the Dess-Martin reaction, and then the carbon chain was extended by the Wittig reaction with bromo(heptadecyl)triphenylphosphine to synthesize 3,11-dimethyl-2,9-octadecan-12-ene.

9. A method for synthesizing 3,11-dimethylnonadec-12-ene, characterized in that: The 3,11-dimethylnonadecane-12-ene is the 3,11-dimethylnonadecane-12-ene according to claim 8; the method for synthesizing 3,11-dimethylnonadecane includes the following steps: 3,11-Dimethylnonadecane was synthesized by Pd / C reduction of 3,11-dimethylnonadecane.

10. A method for synthesizing 3,11-dimethylnonacontane based on 8-tert-butyldiphenylsilyloxy-7-methyloctyl p-toluenesulfonate, characterized in that: The p-toluenesulfonate-8-tert-butyldiphenylsilyloxy-7-methyloctyl ester is the p-toluenesulfonate-8-tert-butyldiphenylsilyloxy-7-methyloctyl ester according to claim 1; the method for synthesizing 3,11-dimethylnonacontane includes the following steps: First, 2,10-dimethyldodecyloxytert-butylsilylsilyloxy-7-methyloctyl ester of p-toluenesulfonate was used as a raw material to synthesize 2,10-dimethyldodecyloxytert-butylsilylsilane. Then, using 2,10-dimethyldodecyloxytert-butyldiphenylsilane as a raw material, 3,11-dimethylnonadecano-12-ene was synthesized. Finally, 3,11-dimethylnonadecane was synthesized from 3,11-dimethylnonadecane.

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