Synthesis method of (5S, 6R)-5, 6-epoxy-2-heptadecene-1-alcohol

Abstract

The invention discloses a synthesis method of (5S, 6R)-5, 6-epoxy-2-heptadecene-1-alcohol, which comprises the following steps: reacting (Z)-1-bromotetradecene with substituted phenyl propargyl ether, performing epoxidation reaction under the action of an epoxidation catalyst, and removing substituted phenyl under the action of an oxidant to obtain (5S, 6R)-5, 6-epoxy-2-heptadecene-1-alcohol. And adding 2, 6-epoxy-2-heptadecene alkyne-1-alcohol into the reaction kettle. The method is mild in synthesis condition, simple and convenient to operate, high in yield, low in preparation cost and good in economic benefit.

Description

Technical Field

[0001] The invention relates to the fields of chemical production technology and biological pesticides, and specifically to a method for synthesizing (5S, 6R)-5,6-epoxy-2-heptadecane-1-ol. Background Art

[0002] The American gypsy moth Hyphantriacunea (Drury) belongs to the Lepidoptera order and the Arctiidae family. It is an important international quarantine pest. It has the characteristics of omnivorous diet, large appetite, strong reproductive ability, wide adaptability, fast spread speed, and serious damage. The American gypsy moth has a wide host range. The tree species it likes to eat include poplar, mulberry, sycamore, white wax maple, etc. In addition, it also harms broad-leaved tree species such as willow, locust, camptotheca, and Ailanthus. In addition to forests and fruit trees, it also harms crops and vegetables; the larvae of the American gypsy moth have a large appetite. When it breaks out, it can eat up the leaves of the entire plant overnight, causing poor growth and development of the plant. In severe cases, it can even cause the death of trees and poor harvests of crops and vegetables, causing serious damage.

[0003] The invasion and spread of the gypsy moth are very diverse. Strengthening pest monitoring is the basic work of preventing and controlling the gypsy moth, and is of great significance for taking timely prevention and control measures to prevent the spread of the epidemic. Among them, using gypsy moth sex traps to trap and monitor male adults is a mature monitoring technology with high accuracy and significant effects.

[0004] The main attractant active ingredients of the sex pheromone of the American white moth are (3Z,6Z,9S,10R)-9,10-epoxy-3,6-heneicosadiene and (3Z,6Z,9S,10R)-9,10-epoxy-1,3,6-heneicostriene. Both of them need to be obtained from the key intermediate (5S,6R)-5,6-epoxy-2-heptadecyn-1-ol (4) through five steps of reaction. The reaction pathway is as follows:

[0005] The key intermediate (5S,6R)-5,6-epoxy-2-heptadecan-1-ol (4) is a white solid at room temperature with a melting point of 69-70°C. Its synthesis method reported in the literature is as follows [J.Org.Chem.2010,75,4619-4622]: In a hexamethylphosphoric acid triamide and ether solvent system, (2S,3R)-2,3-epoxytetradecyl trifluoroacetate and propargyl trimethylsilyl ether are used as raw materials and n-butyl lithium is used as a base to synthesize (5S,6R)-5,6-epoxy-2-heptadecan-1-ol. The (2S,3R)-2,3-epoxytetradecyl trifluoroacetate involved in the reaction is easily deteriorated in the air after purification, is difficult to preserve, and is difficult to achieve large-scale production; therefore, it is of great practical significance to develop an efficient and stable method for synthesizing (5S,6R)-5,6-epoxy-2-heptadecan-1-ol and realize industrial production. Summary of the invention

[0006] The object of the present invention is to provide a method for synthesizing (5S, 6R)-5,6-epoxy-2-heptadecan-1-ol to solve the problems existing in the prior art.

[0007] In order to solve the above technical problems, the present invention provides the following technical solutions: A method for synthesizing (5S,6R)-5,6-epoxy-2-heptadecan-1-ol, comprising reacting (Z)-1-bromotetradecene (1) with substituted phenyl propargyl ether to obtain an intermediate 2, then subjecting the intermediate to an epoxidation reaction under the action of an epoxidation catalyst to obtain an intermediate 3, and then removing the substituted phenyl under the action of an oxidant to obtain (5S,6R)-5,6-epoxy-2-heptadecan-1-ol (4).

[0008] The reaction formula of the synthesis method is: ; Wherein R is hydrogen, C1-4 alkyl or C1-4 alkoxy, and R is a mono-, di-, tri-, tetra- or penta-substituted.

[0009] A method for synthesizing (5S, 6R)-5,6-epoxy-2-heptadecan-1-ol comprises the following steps: (1) in an argon atmosphere, in the presence of cuprous iodide, sodium iodide, cesium carbonate and an organic solvent 1, (Z)-1-bromotetradecene and substituted phenyl propargyl ether are reacted at room temperature. After the reaction is completed, a quenching agent 1 is added to quench the reaction, and the mixture is extracted with an organic extractant 1. The organic phases are combined, washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated to obtain an intermediate 2; (2) The intermediate 2 obtained in step (1), the epoxidation catalyst, and the organic solvent 2 are mixed, and then a buffer solution and a tetrabutylammonium sulfate solution are added. After stirring evenly, a potassium persulfate solution and a potassium carbonate solution are added to react, and a quenching agent 2 is added to quench the reaction. The organic phases are combined, washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated to obtain an intermediate 3; (3) The intermediate 3 and the mixed solvent are mixed, and an oxidant is added to react. After the reaction is completed, (5S,6R)-5,6-epoxy-2-heptadecan-1-ol is obtained by post-treatment.

[0010] As an optimization, the general structural formula of the substituted phenyl propargyl ether in step (1) is: , the number of R is 1 or more, and R is one of hydrogen, methyl, ethyl, isopropyl, and methoxy.

[0011] As an optimization, the organic solvent 1 in step (1) is one of N,N-dimethylformamide and diethyl ether; the quencher 1 is a saturated aqueous solution of ammonium chloride; the volume ratio of the quencher 1 to the organic solvent is 1:1; and the organic extractant 1 is diethyl ether.

[0012] As an optimization, the dispersed concentration of the (Z)-1-bromotetradecene in the organic solvent 1 in step (1) is 0.05-0.5 g / mL, preferably 0.08-0.20 g / mL; the molar ratio of the (Z)-1-bromotetradecene and the substituted phenyl propargyl ether is 1:(1-4); the molar ratio of the (Z)-1-bromotetradecene, sodium iodide, cesium carbonate and cuprous iodide is 1:(1-3):(1-3):(1-3), preferably 1:(1-2):(1-2):(1-2); and the reaction time is 3 h.

[0013] As an optimization, the epoxidation catalyst in step (2) is tert-butyl (3a'R, 5S, 7a'R)-2', 2'-dimethyl-2-7'-dioxotetrahydrospiro[oxazole-5, 6'[1, 3]dioxolane[4, 5c]pyran]-3-carboxylate; the organic solvent 2 is prepared by mixing dimethyl ether and dipropylene glycol dimethyl ether in a volume ratio of 3:1; the buffer solution is prepared by: dissolving potassium carbonate and acetic acid in an ethylenediaminetetraacetic acid solution respectively, and adding the acetic acid in the ethylenediaminetetraacetic acid solution dropwise to the potassium carbonate in the ethylenediaminetetraacetic acid solution, The pH value is adjusted to 8; the tetrabutylammonium sulfate solution is a mixture of tetrabutylammonium sulfate and ethylenediaminetetraacetic acid, and its concentration is 0.005-0.015 g / mL, preferably 0.005-0.01 g / mL; the potassium persulfate solution is a mixture of potassium persulfate and ethylenediaminetetraacetic acid, and its concentration is 0.15-0.25 g / mL, preferably 0.15-0.2 g / mL; the potassium carbonate solution is a mixture of potassium carbonate and ethylenediaminetetraacetic acid; the concentration is 0.3-0.6 g / mL, preferably 0.3-0.4 g / mL.

[0014] As an optimization, the molar ratio of the epoxidation catalyst to the intermediate 2 in step (2) is (5-10):1, preferably (6-7):1; the dispersed concentration of the intermediate 2 in the organic solvent 2 in step (2) is 0.1-0.5 g / mL, preferably 0.12-0.20 g / mL; the molar ratio of the intermediate 2 to tetrabutylammonium sulfate, potassium persulfate, and potassium carbonate is 1:(0.3-0.6):(1.5-3):(3-5), preferably 1:(0.3-0.6):(1.5-3):(3-5); the quencher 2 is n-hexane, and the volume ratio of the quencher 2 to the organic solvent is 1:1; the organic extractant 2 is n-hexane.

[0015] As an optimization, the stirring temperature in step (2) is -10°C; the reaction temperature is -10°C, and the reaction time is 3-6h, preferably 4-5h.

[0016] As an optimization, the mixed solvent in step (3) is water and acetonitrile in a mass ratio of 1:(5-20); the dispersion degree of the intermediate 3 in the mixed solvent is 0.01 g / mL-0.3 g / mL; the oxidant is one of cerium ammonium nitrate, dichlorodicyanobenzoquinone, and potassium monopersulfate; the molar ratio of the oxidant to (Z)-1-bromotetradecene is (3-10):1, the reaction time is 20-50 min, preferably 30-35 min; and the reaction temperature is 0°C.

[0017] As an optimization, the post-treatment step of step (3) is: adding saturated sodium bicarbonate aqueous solution with a volume of 1.5-4.0 times of the mixed solvent to quench the reaction, using ethyl acetate for extraction, combining the organic phases, washing with saturated brine, drying over anhydrous magnesium sulfate and concentrating, and purifying by column chromatography. The eluent for column chromatography purification is obtained by mixing petroleum ether and ethyl acetate in a volume ratio of (5-20):1.

[0018] Compared with the prior art, the beneficial effects achieved by the present invention are: (1) Substituted phenyl propargyl ether containing a benzene ring structure is reacted with (Z)-1-bromotetradecene to form an intermediate 2 containing a benzene ring structure, which has a large difference in polarity from the intermediate 3 produced by the subsequent ring-closing reaction, which is convenient for monitoring the reaction in actual production.

[0019] (2) The method for synthesizing (5S,6R)-5,6-epoxy-2-heptadecan-1-ol provided by the present invention does not require column chromatography purification after the reaction of step (1) and step (2), and only requires simple post-treatment to obtain a high-yield product. The three-step reaction is similar to a "one-pot" treatment method to obtain the final product (5S,6R)-5,6-epoxy-2-heptadecan-1-ol, which reduces the loss in the purification process, is simple to operate, and is suitable for large-scale production; (3) The reaction conditions for de-substituted phenyl groups by ammonium cerium nitrate are mild and controllable, and the yield is good. BRIEF DESCRIPTION OF THE DRAWINGS

[0020] Figure 1 This is the NMR detection spectrum of (5S,6R)-5,6-epoxy-2-heptadecan-1-ol prepared in Example 1; wherein the abscissa is the chemical shift in ppm; the ordinate is the signal intensity; and the data under the peak in the spectrum is the integrated area of ​​the peak. DETAILED DESCRIPTION

[0021] The following will be combined with the embodiments of the present invention to clearly and completely describe the technical solutions in the embodiments of the present invention. Obviously, the described embodiments are only part of the embodiments of the present invention, not all of the embodiments. Based on the embodiments of the present invention, all other embodiments obtained by ordinary technicians in this field without making creative work are within the scope of protection of the present invention.

[0022] The epoxidation catalyst used in the following examples is tert-butyl (3a'R, 5S, 7a'R)-2', 2'-dimethyl-2-7'-dioxotetrahydrospiro[oxazole-5, 6'[1, 3]dioxolane[4, 5c]pyran]-3-carboxylate; the organic solvent 2 is obtained by mixing dimethyl ether and dipropylene glycol dimethyl ether in a volume ratio of 3:1; the buffer solution used is prepared by: potassium carbonate and acetic acid are respectively dissolved in an ethylenediaminetetraacetic acid solution, and the acetic acid ethylenediaminetetraacetic acid solution is added dropwise to the potassium carbonate ethylenediaminetetraacetic acid solution, and the pH is adjusted to 8; the eluent used for column chromatography purification is obtained by mixing petroleum ether and ethyl acetate in a volume ratio of 10:1. Embodiment 1:

[0023] A method for synthesizing (5S, 6R)-5,6-epoxy-2-heptadecan-1-ol, the method comprising the following steps: (1) Dissolve 0.76 g of cuprous iodide, 0.60 g of sodium iodide, and 1.30 g of cesium carbonate in 15 mL of N,N-dimethylformamide, add dropwise a solution of 0.64 g of phenyl propargyl ether in 5 mL of N,N-dimethylformamide, stir thoroughly after the addition is complete, then add dropwise a solution of 1.08 g of (Z)-1-bromotetradecene in 5 mL of N,N-dimethylformamide, react at room temperature for 3 h, add dropwise 25 mL of saturated aqueous ammonium chloride to quench the reaction, extract with ether, combine the organic phases, wash once with saturated brine, dry over anhydrous magnesium sulfate, filter, and concentrate to obtain intermediate 2; (2) Dissolve the intermediate 2 and 0.185 g of the epoxidation catalyst in 10 mL of the organic solvent 2, add 6 mL of the buffer solution and 5 mL of the ethylenediaminetetraacetic acid solution of 0.033 g of tetrabutylammonium sulfate, stir at -10°C, then dropwise add 20 mL of the ethylenediaminetetraacetic acid solution of 3.95 g of potassium persulfate and 5 mL of the ethylenediaminetetraacetic acid solution of 2 g of potassium carbonate. After the addition is complete, react at -10°C for 4 h, add 60 mL of n-hexane to quench the reaction, extract with n-hexane, combine the organic phases, wash once with a saturated saline solution, dry over anhydrous magnesium sulfate, and concentrate to obtain the intermediate 3; (3) The intermediate 3 was dissolved in a mixed solvent of acetonitrile / water (30 mL / 3 mL), cooled to 0°C, and 4.63 g of cerium ammonium nitrate was added. The mixture was stirred for 0.5 h, and 60 mL of saturated sodium bicarbonate aqueous solution was added to quench the reaction. The mixture was extracted with ethyl acetate, and the organic phases were combined, washed once with saturated brine, dried over anhydrous magnesium sulfate, concentrated, and purified by column chromatography to obtain 0.79 g of (5S,6R)-5,6-epoxy-2-heptadecan-1-ol in a yield of 68%.

[0024] Comparative Example 1: A method for synthesizing (5S, 6R)-5,6-epoxy-2-heptadecan-1-ol, the method comprising the following steps: (1) 0.76 g of cuprous iodide, 0.6 g of sodium iodide, and 1.3 g of cesium carbonate were dissolved in 15 mL of N,N-dimethylformamide, and a solution of 0.64 g of p-methoxyphenyl propargyl ether in 5 mL of N,N-dimethylformamide was added dropwise. After the addition was completed, the mixture was stirred thoroughly, and a solution of 1.08 g of (Z)-1-bromotetradecene in 5 mL of N,N-dimethylformamide was added dropwise. The mixture was reacted at room temperature for 3 h, and 25 mL of saturated aqueous ammonium chloride solution was added dropwise to quench the reaction. The mixture was extracted with ether, and the organic phases were combined, washed once with saturated brine, dried over anhydrous magnesium sulfate, concentrated, and purified by column chromatography to obtain 1.28 g of intermediate 2 with a yield of 90%. The characterization data are as follows: 1HNMR(400MHz,Chloroform-d)δ6.94(ddd,J=9.3,4.7,2.2Hz,2H),6.89–6.80(m,2H),5.82–5.60(m,1H),5.53–5.35(m,1H),4.72–4 .58(m,2H),3.79(s,3H),3.16–2.92(m,2H),2.03(t,J=7.9Hz,1H),1.56–1.45(m,1H),1.28(d,J=3.8Hz,19H),0.91(t,J=6.7Hz,3H); (2) 1.28 g of intermediate 2 and 0.185 g of epoxidation catalyst were dissolved in 10 mL of organic solvent 2, 6 mL of buffer solution and 5 mL of ethylenediaminetetraacetic acid solution of 0.033 g of tetrabutylammonium sulfate were added, the mixture was placed at -10°C and stirred thoroughly, 20 mL of ethylenediaminetetraacetic acid aqueous solution of 3.95 g of potassium persulfate and 5 mL of ethylenediaminetetraacetic acid aqueous solution of 2 g of potassium carbonate were added dropwise, after the addition was completed, the mixture was reacted at -10°C for 4 h, 60 mL of n-hexane was added to quench the reaction, and the n-hexane was extracted. The organic phases were combined, washed once with saturated saline solution, dried over anhydrous magnesium sulfate, concentrated, and purified by column chromatography to obtain 1.19 g of intermediate 3 with a yield of 89%; the characterization data are as follows: 1HNMR(400MHz,Chloroform-d)δ6.98–6.90(m,2H),6.89–6.81(m,2H),4.65(t,J=2.2Hz,2H),3.79(s,3H),3.15(ddd,J=7.0,5.6,4.1Hz,1H),2 .97(td,J=5.9,4.0Hz,1H),2.64(ddt,J=17.2,5.7,2.2Hz,1H),2.36(ddt,J=17.2,7.0,2.2Hz,1H),1.57–1.18(m,21H),0.90(t,J=6.7Hz,3H); 1.19 g of intermediate 3 was dissolved in a mixed solvent of acetonitrile / water (10 mL / 1 mL), cooled to 0 °C, 4.63 g of cerium ammonium nitrate was added, stirred for 0.5 h, 40 mL of saturated sodium bicarbonate aqueous solution was added to quench the reaction, extracted with ethyl acetate, the organic phases were combined, washed once with saturated brine, dried over anhydrous magnesium sulfate, concentrated, and purified by column chromatography to obtain 1.08 g of (5S, 6R)-5,6-epoxy-2-heptadecan-1-ol, with a yield of 93%. Characterization data are as follows: 1HNMR(400MHz,Chloroform-d)δ4.29(t,J=2.2Hz,2H),3.16(ddd,J=6.8,5.8,4.1Hz,1H),2.99(td,J=5.9,4.1Hz,1 H),2.62(ddt,J=17.1,5.8,2.2Hz,1H),2.37(ddt,J=17.1,6.9,2.2Hz,1H),1.56–1.10(m,21H),0.98–0.83(m,3H).

[0025] Comparative Example 2: A method for synthesizing (5S, 6R)-5,6-epoxy-2-heptadecan-1-ol, the method comprising the following steps: (1) 2.28 g of cuprous iodide, 1.80 g of sodium iodide, and 3.90 g of cesium carbonate were dissolved in 45 mL of N,N-dimethylformamide, and a solution of 1.92 g of phenyl propargyl ether in 15 mL of N,N-dimethylformamide was added dropwise. After the addition was complete, the mixture was stirred thoroughly, and a solution of 3.24 g of (Z)-1-bromotetradecene in 15 mL of N,N-dimethylformamide was added dropwise. The mixture was reacted at room temperature for 3 h, and 75 mL of saturated aqueous ammonium chloride solution was added dropwise to quench the reaction. The mixture was extracted with ether, and the organic phases were combined, washed once with saturated brine, dried over anhydrous magnesium sulfate, concentrated, and purified by column chromatography to obtain 3.72 g of intermediate 2 with a yield of 87%. The characterization data are as follows: 1H NMR(400MHz,Chloroform-d)δ6.94(ddd,J=9.3,4.7,2.2Hz,2H),6.89–6.80(m,2H),5.82–5.60(m,1H),5.53–5.35(m,1H),4.72–4. 58(m,2H),3.79(s,3H),3.16–2.92(m,2H),2.03(t,J=7.9Hz,1H),1.56–1.45(m,1H),1.28(d,J=3.8Hz,19H),0.91(t,J=6.7Hz,3H); (2) 3.72 g of the intermediate 2 synthesized in Example 1 and 0.54 g of the epoxidation catalyst were dissolved in 30 mL of the organic solvent 2, 18 mL of the buffer solution and 15 mL of the ethylenediaminetetraacetic acid solution of 0.10 g of tetrabutylammonium sulfate were added, the mixed solution was placed at -10°C and stirred thoroughly, and then 60 mL of the ethylenediaminetetraacetic acid solution of 11.42 g of potassium persulfate and 15 mL of the ethylenediaminetetraacetic acid solution of 5.80 g of potassium carbonate were added dropwise. After the addition was complete, the mixture was reacted at -10°C for 4 h, 180 mL of n-hexane was added to quench the reaction, and the n-hexane was extracted. The organic phases were combined, washed once with a saturated saline solution, dried over anhydrous magnesium sulfate, concentrated, and purified by column chromatography to obtain 3.34 g of the intermediate 3 with a yield of 86%. The characterization data are as follows: 1HNMR(400MHz,Chloroform-d)δ6.98–6.90(m,2H),6.89–6.81(m,2H),4.65(t,J=2.2Hz,2H),3.79(s,3H),3.15(ddd,J=7.0,5.6,4.1Hz,1H),2 .97(td,J=5.9,4.0Hz,1H),2.64(ddt,J=17.2,5.7,2.2Hz,1H),2.36(ddt,J=17.2,7.0,2.2Hz,1H),1.57–1.18(m,21H),0.90(t,J=6.7Hz,3H); (3) 3.34 g of intermediate 3 was dissolved in a mixed solvent of acetonitrile / water (10 mL / 1 mL), cooled to 0 °C, and 9.51 g of cerium ammonium nitrate was added. The mixture was stirred for 0.5 h, and the reaction was quenched with 40 mL of saturated sodium bicarbonate aqueous solution. The mixture was extracted with ethyl acetate, and the organic phases were combined, washed once with saturated brine, dried over anhydrous magnesium sulfate, concentrated, and purified by column chromatography to obtain 2.24 g of (5S,6R)-5,6-epoxy-2-heptadecan-1-ol in a yield of 94%.

[0026] The specific implementation methods described above further illustrate the objectives, technical solutions and beneficial effects of the present invention in detail. It should be understood that the above description is only a specific implementation method of the present invention and is not intended to limit the scope of protection of the present invention. Any modifications, equivalent substitutions, improvements, etc. made within the spirit and principles of the present invention should be included in the scope of protection of the present invention.

Claims

1. A method for synthesizing (5S,6R)-5,6-epoxy-2-heptadecan-1-ol, characterized in that: The synthesis method comprises reacting (Z)-1-bromotetradecene (1) with substituted phenyl propargyl ether to obtain intermediate 2, then performing epoxidation reaction under the action of an epoxidation catalyst to obtain intermediate 3, and then removing the substituted phenyl under the action of an oxidant to obtain (5S,6R)-5,6-epoxy-2-heptadecan-1-ol (4); The reaction formula of the synthesis method is: ； Where R is hydrogen, C 1-4 Alkyl or C 1-4 Alkoxy, R is a mono-, di-, tri-, tetra- or penta-substituted group.

2. The method for synthesizing (5S,6R)-5,6-epoxy-2-heptadecyne-1-ol according to claim 1, characterized in that: The following steps are involved: (1) in an argon atmosphere, in the presence of cuprous iodide, sodium iodide, cesium carbonate and an organic solvent 1, (Z)-1-bromotetradecene and substituted phenyl propargyl ether are reacted at room temperature. After the reaction is completed, a quenching agent 1 is added to quench the reaction, and the mixture is extracted with an organic extractant 1. The organic phases are combined, washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated to obtain an intermediate 2; (2) The intermediate 2 obtained in step (1), the epoxidation catalyst, and the organic solvent 2 are mixed, and then a buffer solution and a tetrabutylammonium sulfate solution are added. After stirring evenly, a potassium persulfate solution and a potassium carbonate solution are added to react, and a quenching agent 2 is added to quench the reaction. The organic phases are combined, washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated to obtain an intermediate 3; (3) The intermediate 3 and the mixed solvent are mixed, and an oxidant is added to react. After the reaction is completed, (5S,6R)-5,6-epoxy-2-heptadecan-1-ol is obtained by post-treatment.

3. The method for synthesizing (5S,6R)-5,6-epoxy-2-heptadecyne-1-ol according to claim 2, characterized in that: The general structural formula of the substituted phenyl propargyl ether in step (1) is: , the number of R is 1 or more, and R is one of hydrogen, methyl, ethyl, isopropyl, and methoxy.

4. The method for synthesizing (5S,6R)-5,6-epoxy-2-heptadecyne-1-ol according to claim 2, characterized in that: In step (1), the organic solvent 1 is one of N,N-dimethylformamide and diethyl ether; the quencher 1 is a saturated aqueous solution of ammonium chloride; the volume ratio of the quencher 1 to the organic solvent is 1:1; and the organic extractant 1 is diethyl ether.

5. The method for synthesizing (5S,6R)-5,6-epoxy-2-heptadecyne-1-ol according to claim 2, characterized in that: The dispersed concentration of the (Z)-1-bromotetradecene in the organic solvent 1 in step (1) is 0.05-0.5 g / mL, preferably 0.08-0.20 g / mL; the molar ratio of the (Z)-1-bromotetradecene to the substituted phenyl propargyl ether is 1:(1-4); the molar ratio of the (Z)-1-bromotetradecene, sodium iodide, cesium carbonate and cuprous iodide is 1:(1-3):(1-3):(1-3), preferably 1:(1-2):(1-2):(1-2); and the reaction time is 3 hours.

6. The method for synthesizing (5S,6R)-5,6-epoxy-2-heptadecyne-1-ol according to claim 2, characterized in that: The epoxidation catalyst in step (2) is tert-butyl (3a'R, 5S, 7a'R)-2', 2'-dimethyl-2-7'-dioxotetrahydrospiro[oxazole-5, 6'[1, 3]dioxolane[4, 5c]pyran]-3-carboxylate; the organic solvent 2 is prepared by mixing dimethyl ether and dipropylene glycol dimethyl ether in a volume ratio of 3:1; the buffer solution is prepared by: dissolving potassium carbonate and acetic acid in an ethylenediaminetetraacetic acid solution, respectively, adding the acetic acid solution in ethylenediaminetetraacetic acid dropwise to the potassium carbonate solution in ethylenediaminetetraacetic acid, and adjusting the to pH=8; the tetrabutylammonium sulfate solution is formed by mixing tetrabutylammonium sulfate and ethylenediaminetetraacetic acid, and its concentration is 0.005-0.015 g / mL, preferably 0.005-0.01 g / mL; the potassium persulfate solution is formed by mixing potassium persulfate and ethylenediaminetetraacetic acid, and its concentration is 0.15-0.25 g / mL, preferably 0.15-0.2 g / mL; the potassium carbonate solution is formed by mixing potassium carbonate and ethylenediaminetetraacetic acid; the concentration is 0.3-0.6 g / mL, preferably 0.3-0.4 g / mL.

7. The method for synthesizing (5S,6R)-5,6-epoxy-2-heptadecyne-1-ol according to claim 2, characterized in that: The molar ratio of the epoxidation catalyst to the intermediate 2 in step (2) is (5-10):1, preferably (6-7):1; the dispersed concentration of the intermediate 2 in the organic solvent 2 in step (2) is 0.1-0.5 g / mL, preferably 0.12-0.20 g / mL; the molar ratio of the intermediate 2 to tetrabutylammonium sulfate, potassium persulfate, and potassium carbonate is 1:(0.3-0.6):(1.5-3):(3-5), preferably 1:(0.3-0.6):(1.5-3):(3-5); the quencher 2 is n-hexane, and the volume ratio of the quencher 2 to the organic solvent is 1:6; the organic extractant 2 is n-hexane.

8. The method for synthesizing (5S,6R)-5,6-epoxy-2-heptadecyne-1-ol according to claim 2, characterized in that: The stirring temperature in step (2) is -10°C; the reaction temperature is -10°C, and the reaction time is 3-6h, preferably 4-5h.

9. The method for synthesizing (5S,6R)-5,6-epoxy-2-heptadecyne-1-ol according to claim 2, characterized in that: The mixed solvent of step (3) is water and acetonitrile in a mass ratio of 1:(5-20); the dispersion degree of the intermediate 3 in the mixed solvent is 0.01 g / mL-0.3 g / mL; the oxidant is one of cerium ammonium nitrate, dichlorodicyanobenzoquinone, and potassium monopersulfate; the molar ratio of the oxidant to (Z)-1-bromotetradecene is (3-10):1, the reaction time is 20-50 min, preferably 30-35 min; and the reaction temperature is 0°C.

10. The method for synthesizing (5S,6R)-5,6-epoxy-2-heptadecyne-1-ol according to claim 2, characterized in that: The post-treatment step in step (3) is as follows: adding saturated sodium bicarbonate aqueous solution with a volume of 1.5-4.0 times of the mixed solvent to quench the reaction, extracting with ethyl acetate, combining the organic phases, washing with saturated brine, drying with anhydrous magnesium sulfate, and concentrating, and purifying by column chromatography. The eluent for column chromatography purification is obtained by mixing petroleum ether and ethyl acetate in a volume ratio of (5-20):1.

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