CN115197185A - Preparation method of transition metal catalyzed pyranoside derivative - Google Patents

Preparation method of transition metal catalyzed pyranoside derivative Download PDF

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CN115197185A
CN115197185A CN202110388197.0A CN202110388197A CN115197185A CN 115197185 A CN115197185 A CN 115197185A CN 202110388197 A CN202110388197 A CN 202110388197A CN 115197185 A CN115197185 A CN 115197185A
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transition metal
acetylacetonate
deionized water
isopropanol
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路芳
卢锐
司晓勤
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Dalian Institute of Chemical Physics of CAS
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D309/10—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H1/00—Processes for the preparation of sugar derivatives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/26—Acyclic or carbocyclic radicals, substituted by hetero rings
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Abstract

The invention discloses a preparation method of a pyranoside derivative catalyzed by transition metal. In particular to a method for preparing pyranoside derivatives by one-step dehydration coupling reaction of carbohydrates and the like serving as raw materials and isopropanol in a mixed solvent system of deionized water and a dipolar aprotic solvent under the action of a transition metal catalyst. The method has the advantages of short route, mild conditions, high atom economy and good application prospect.

Description

Preparation method of transition metal catalyzed pyranoside derivative
Technical Field
The invention relates to the fields of organic synthesis, fine chemical industry, medicine, daily cosmetics and the like, relates to a preparation method of a pyranoside derivative catalyzed by a transition metal, and particularly relates to a method for obtaining the pyranoside derivative in one step by taking carbohydrate and isopropanol as raw materials and performing a dehydration coupling reaction under the action of a transition metal catalyst.
Background
The glucoside compound has important biological activity, and can be widely applied to the industries of medicine and cosmetics. The C-glycoside is an O-glycoside analogue in which the oxygen atom on the glycosidic bond is replaced by a methylene group, so that the C-glycoside molecule has good stability to acid and enzyme catalytic hydrolysis due to the fact that the oxygen atom of the glycoside is replaced by the methylene group. Currently, only limited C-glycoside synthesis methods are disclosed, and most require a hydrogenation step to obtain the final target product. CN202010629023.4 discloses a method for preparing C-pyranoside, namely boscalid, by using a biological enzyme one-pot method, and specifically, xylose and isopropanol are used as substrates, and corresponding C-pyranoside is generated under the catalytic action of isopropanol dehydrogenase, boscalid synthetase, carbonyl reductase and coenzyme nicotinamide adenine dinucleotide. However, the process needs the synergistic effect of multiple enzyme catalysts, and has the disadvantages of long flow, low efficiency, high cost and difficulty in realizing large-scale production. Therefore, the development of a simple, efficient and low-cost preparation method of the C-glycoside derivative is very important for the application of the C-glycoside derivative in the fields of medicine, cosmetic industry and the like.
Disclosure of Invention
The invention aims to provide a method for one-step obtaining pyranoside derivatives by taking carbohydrate and isopropanol as raw materials and performing dehydration coupling reaction under the action of a transition metal catalyst.
In order to achieve the purpose, the technical scheme adopted by the invention is as follows:
the specific process method comprises the following steps: mixing a mixture of 1:10 to 10: dissolving a carbohydrate and isopropanol reaction raw material of 1 in a mixed solvent system of deionized water and a dipolar aprotic solvent (the mass ratio of the carbohydrate and the mixed solvent is 1; the examples of the present invention were subjected to performance evaluation and process condition testing in a stainless steel reaction vessel, but are not limited to the stainless steel reaction vessel.
The carbohydrate is selected from one of glucose, mannose, galactose, xylose, arabinose, lactose, maltose and cellobiose;
the transition metal catalyst is selected from at least one of ferric acetylacetonate, nickel acetylacetonate, cobalt acetylacetonate, vanadyl acetylacetonate, molybdenum acetylacetonate, ruthenium acetylacetonate, vanadyl sulfate, ammonium metavanadate, ammonium molybdate, methyl rhenium trioxide, rhenium heptoxide, ammonium perrhenate, molybdenum hexacarbonyl, tungsten hexacarbonyl, ferrocene, cobaltocene, nickelocene and ruthenium triphenylphosphine chloride;
the dipolar aprotic solvent is selected from at least one of acetonitrile, acetone, N, N-dimethyl sulfoxide, N, N-dimethylformamide, N, N-dimethylacetamide and hexamethylphosphoramide.
Optionally, the lower limit of the molar ratio of carbohydrate feedstock to isopropanol is selected from the group consisting of 1, 1:5, 2:5, 3:5, 1:1; the upper limit is selected from the group consisting of 10, 5:1, 5:2, 5:3, 1:1;
optionally, the lower limit of the volume ratio of the deionized water to the dipolar aprotic solvent in the mixed solvent system is selected from the group consisting of 1; the upper limit is selected from 2:1, 3:2, 1:1;
optionally, the lower limit of the molar ratio of the transition metal catalyst to the carbohydrate feedstock of the saccharide is selected from 1; the upper limit is selected from 1;
optionally, the reaction temperature is 120 ℃.
Compared with the route of the prior art, the method has the following characteristics:
the invention provides a method for one-step obtaining pyranoside derivatives by taking carbohydrate and isopropanol as raw materials and carrying out dehydration coupling reaction under the action of a transition metal catalyst. The method has the advantages of simple process, strong operability, wide raw material source, recoverable catalyst and considerable large-scale prospect.
Detailed Description
The present application will be described in detail with reference to examples, but the present application is not limited to these examples.
Unless otherwise specified, the raw materials and catalysts in the examples of the present application were all purchased commercially.
Saccharides such as glucose and maltose are available from Shanghai Aladdin Biotechnology Ltd.
Transition metal complex catalysts such as cobalt acetylacetonate, vanadyl acetylacetonate, molybdenum hexacarbonyl, and the like are commercially available from the national pharmaceutical group chemical agents ltd.
Dipolar aprotic solvents such as acetonitrile, N-dimethyl sulfoxide, N-dimethylformamide and the like are available from chemicals of the national chemical group ltd.
The yield of the product pyranoside derivative was calculated according to the following formula:
Figure BDA0003015788930000031
example 1
Figure BDA0003015788930000032
Completely dissolving 1.80kg of glucose in 6.00L of a deionized water and acetonitrile mixed solvent (the volume ratio of the deionized water to the acetonitrile is 1:1), transferring the solution into a 20L stainless steel reaction kettle, pumping 0.90kg of isopropanol into the reaction kettle by using a peristaltic pump while stirring, and uniformly mixing. Then 0.24kg of transition metal catalyst vanadyl acetylacetonate is added, the reaction kettle is sealed and stirred, the temperature is raised to 120 ℃, the reaction is stopped after 12 hours, reaction liquid is collected, the solvent and excessive isopropanol are removed by reduced pressure distillation, 1L of deionized water is added to dissolve and filter the catalyst, ethyl acetate is used for extraction for three times (the dosage is 0.25L each time) to remove residual byproducts, water phase is collected, reduced pressure distillation is carried out, vacuum drying is carried out for 12 hours at 40 ℃, and 0.81kg of target product C-glucopyranoside derivative is obtained, wherein the yield is 36.5%.
Example 2
Figure BDA0003015788930000041
Completely dissolving 1.80kg of glucose in 6.00L of a deionized water and acetonitrile mixed solvent (the volume ratio of the deionized water to the acetonitrile is 1:1), transferring the solution into a 20L stainless steel reaction kettle, pumping 0.90kg of isopropanol into the reaction kettle by using a peristaltic pump while stirring, and uniformly mixing. And adding 0.18kg of transition metal catalyst ammonium molybdate, sealing the reaction kettle, stirring, heating to 120 ℃, stopping the reaction after 12 hours of reaction, collecting the reaction liquid, distilling under reduced pressure to remove the solvent and excessive isopropanol, adding 1L of deionized water to dissolve and filter to remove the catalyst, extracting with ethyl acetate for three times (0.25L of each dosage), removing residual byproducts, collecting the water phase, distilling under reduced pressure, and drying under vacuum at 40 ℃ for 12 hours to obtain 0.53kg of the target product C-glucopyranoside derivative, wherein the yield is 23.9%.
Example 3
Figure BDA0003015788930000042
Completely dissolving 1.80kg of glucose in 6.00L of a deionized water and acetonitrile mixed solvent (the volume ratio of the deionized water to the acetonitrile is 1:1), transferring the solution into a 20L stainless steel reaction kettle, pumping 0.90kg of isopropanol into the reaction kettle by using a peristaltic pump while stirring, and uniformly mixing. Then 0.23kg of transition metal catalyst methyl rhenium trioxide is added, the reaction kettle is sealed and stirred, the temperature is raised to 120 ℃, the reaction is stopped after 12 hours, the reaction liquid is collected, the solvent and excessive isopropanol are removed by reduced pressure distillation, 1L of deionized water is added for dissolving and filtering to remove the catalyst, ethyl acetate is used for extraction for three times (the dosage is 0.25L each time) to remove the residual by-products, the water phase is collected, reduced pressure distillation is carried out, vacuum drying is carried out for 12 hours at 40 ℃, and the target product C-glucopyranoside derivative is obtained, wherein the yield is 0.91kg, and the yield is 41.0%.
Example 4
Figure BDA0003015788930000051
Completely dissolving 1.80kg of glucose in 6.00L of a deionized water and acetonitrile mixed solvent (the volume ratio of the deionized water to the acetonitrile is 1:1), transferring the solution into a 20L stainless steel reaction kettle, pumping 0.90kg of isopropanol into the reaction kettle by using a peristaltic pump while stirring, and uniformly mixing. Then 0.08kg of transition metal catalyst triphenylphosphine ruthenium chloride is added, the reaction kettle is sealed and stirred, the temperature is raised to 120 ℃, the reaction is stopped after 12 hours, reaction liquid is collected, the solvent and excessive isopropanol are removed through reduced pressure distillation, 1L of deionized water is added for dissolving and filtering to remove the catalyst, ethyl acetate is used for extraction for three times (the dosage is 0.25L each time), residual byproducts are removed, water phase is collected, reduced pressure distillation is carried out, vacuum drying is carried out for 12 hours at 40 ℃, and the target product C-glucopyranoside derivative 1.21kg is obtained, and the yield is 54.5%.
Example 5
Figure BDA0003015788930000052
Completely dissolving 1.80kg of glucose in 6.00L of a deionized water and acetonitrile mixed solvent (the volume ratio of the deionized water to the acetonitrile is 1:1), transferring the solution into a 20L stainless steel reaction kettle, pumping 0.90kg of isopropanol into the reaction kettle by using a peristaltic pump while stirring, and uniformly mixing. And adding 0.30kg of transition metal catalyst molybdenum acetylacetonate, sealing the reaction kettle, stirring, heating to 120 ℃, stopping the reaction after 12 hours of reaction, collecting reaction liquid, distilling under reduced pressure to remove the solvent and excessive isopropanol, adding 1L of deionized water to dissolve and filter to remove the catalyst, extracting with ethyl acetate for three times (the dosage is 0.25L each time), removing residual byproducts, collecting a water phase, distilling under reduced pressure, and drying under vacuum at 40 ℃ for 12 hours to obtain 1.53kg of the target product C-glucopyranoside derivative, wherein the yield is 68.9%.
Example 6
Figure BDA0003015788930000061
Completely dissolving 1.80kg of glucose in 6.00L of deionized water and N, N-dimethylformamide mixed solvent (the volume ratio of the deionized water to the N, N-dimethylformamide is 1:1), transferring to a 20L stainless steel reaction kettle, pumping 0.90kg of isopropanol into the reaction kettle by using a peristaltic pump while stirring, and uniformly mixing. And then 0.30kg of transition metal catalyst molybdenum acetylacetonate is added, the reaction kettle is sealed and stirred, the temperature is raised to 120 ℃, the reaction is stopped after 12 hours, reaction liquid is collected, the solvent and excessive isopropanol are removed by reduced pressure distillation, 1L of deionized water is added to dissolve and filter the catalyst, ethyl acetate is used for extraction for three times (the dosage is 0.25L each time) to remove residual byproducts, water phase is collected, reduced pressure distillation is carried out, vacuum drying is carried out for 12 hours at the temperature of 40 ℃, and 1.05kg of the target product C-glucopyranoside derivative is obtained, wherein the yield is 47.3%.
Example 7
Figure BDA0003015788930000062
Completely dissolving 1.80kg of glucose in 6.00L of a mixed solvent of deionized water and acetone (the volume ratio of the deionized water to the acetone is 1:1), transferring the solution into a 20L stainless steel reaction kettle, pumping 0.90kg of isopropanol into the reaction kettle by using a peristaltic pump while stirring, and uniformly mixing. Then 0.30kg of transition metal catalyst molybdenum acetylacetonate is added, the reaction kettle is sealed and stirred, the temperature is raised to 120 ℃, the reaction is stopped after 12 hours, the reaction liquid is collected, the solvent and excessive isopropanol are removed by reduced pressure distillation, 1L of deionized water is added for dissolving and filtering to remove the catalyst, ethyl acetate is used for extraction for three times (the dosage is 0.25L each time) to remove the residual by-product, the water phase is collected, reduced pressure distillation is carried out, vacuum drying is carried out for 12 hours at the temperature of 40 ℃, and the target product C-glucopyranoside derivative 1.15kg is obtained, and the yield is 51.8 percent.
Example 8
Figure BDA0003015788930000071
Completely dissolving 1.80kg of glucose in 6.00L of deionized water and acetonitrile mixed solvent (the volume ratio of the deionized water to the acetonitrile is 1:3), transferring the solution into a 20L stainless steel reaction kettle, pumping 0.90kg of isopropanol into the reaction kettle by using a peristaltic pump while stirring, and uniformly mixing. And adding 0.30kg of transition metal catalyst molybdenum acetylacetonate, sealing the reaction kettle, stirring, heating to 120 ℃, stopping the reaction after 12 hours of reaction, collecting reaction liquid, distilling under reduced pressure to remove the solvent and excessive isopropanol, adding 1L of deionized water to dissolve and filter to remove the catalyst, extracting with ethyl acetate for three times (the dosage is 0.25L each time), removing residual byproducts, collecting a water phase, distilling under reduced pressure, and drying under vacuum at 40 ℃ for 12 hours to obtain 2.00kg of the target product C-glucopyranoside derivative, wherein the yield is 90.1%.
Example 9
Figure BDA0003015788930000072
3.42kg of maltose is completely dissolved in 6.00L of deionized water and acetonitrile mixed solvent (the volume ratio of the deionized water to the acetonitrile is 1:3), transferred into a 20L stainless steel reaction kettle, and 0.90kg of isopropanol is pumped into the reaction kettle by a peristaltic pump while stirring, and is uniformly mixed. Then 0.30kg of transition metal catalyst molybdenum acetylacetonate is added, the reaction kettle is sealed and stirred, the temperature is raised to 120 ℃, the reaction is stopped after 12 hours, the reaction liquid is collected, the solvent and excessive isopropanol are removed by reduced pressure distillation, 1L of deionized water is added for dissolving and filtering to remove the catalyst, ethyl acetate is used for extraction for three times (the dosage is 0.25L each time) to remove the residual by-product, the water phase is collected, reduced pressure distillation is carried out, vacuum drying is carried out for 12 hours at the temperature of 40 ℃, and the target product C-maltopyranoside derivative 3.21kg is obtained, and the yield is 83.6 percent.
In conclusion, the application provides a preparation method of the pyranoside derivative, which is a method for obtaining the pyranoside derivative by taking saccharide carbohydrate and isopropanol as raw materials and promoting one-step reaction through a transition metal catalyst, and has higher atom economy. The raw material source is wide, and the catalyst can be recovered. Simple process, mild condition, strong operability and large-scale prospect.
Although the present invention has been described with reference to a few preferred embodiments, it should be understood that various changes and modifications can be made without departing from the spirit and scope of the invention as defined by the appended claims.

Claims (10)

1. A preparation method of a transition metal catalyzed pyranoside derivative is characterized by comprising the following steps: at least comprises the following steps: the pyranoside derivative is obtained by one-step dehydration coupling reaction of a raw material containing carbohydrate and isopropanol in a mixed solvent system of deionized water and a dipolar aprotic solvent under the action of a transition metal catalyst.
2. The method of claim 1, wherein: the carbohydrate is selected from one of glucose, mannose, galactose, xylose, arabinose, lactose, maltose and cellobiose.
3. The method of claim 1, wherein: the transition metal catalyst is selected from at least one of iron acetylacetonate, nickel acetylacetonate, cobalt acetylacetonate, vanadyl acetylacetonate, molybdenum acetylacetonate, ruthenium acetylacetonate, vanadyl sulfate, ammonium metavanadate, ammonium molybdate, methyl rhenium trioxide, rhenium heptoxide, ammonium perrhenate, molybdenum hexacarbonyl, tungsten hexacarbonyl, ferrocene, cobaltocene, nickelocene and ruthenium triphenylphosphine chloride.
4. The method of claim 1, wherein: the dipolar aprotic solvent is selected from at least one of acetonitrile, acetone, N, N-dimethyl sulfoxide, N, N-dimethylformamide, N, N-dimethylacetamide and hexamethylphosphoramide.
5. The method of claim 1, wherein: at least comprises the following steps: dissolving carbohydrate in a mixed solvent system of deionized water and a dipolar aprotic solvent, sequentially adding isopropanol and a transition metal catalyst, after the reaction is finished, carrying out reduced pressure distillation, filtering, extracting with ethyl acetate, collecting a water phase, carrying out reduced pressure distillation again, and carrying out vacuum drying to obtain the pyranoside derivative.
6. The method of claim 1, wherein: the molar ratio of the carbohydrate raw material to the isopropanol is 1:10 to 10:1.
7. the method of claim 1, wherein: the volume ratio of the deionized water to the dipolar aprotic solvent in the mixed solvent system is 1:10 to 10:1.
8. the method of claim 1, wherein: the molar ratio of the dosage of the transition metal catalyst to the carbohydrate raw material is 1:1000 to 1:10.
9. the method of claim 1, wherein: the reaction temperature is 30-200 ℃;
preferably 120 deg.c.
10. The production method according to claim 1, characterized in that: the reaction time is 0.5 to 12 hours.
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CN108883122A (en) * 2016-03-11 2018-11-23 菲姆布里昂医疗公司 There are the C- glycoside compounds for treating disease
CN111559998A (en) * 2020-05-20 2020-08-21 铭颜生物科技(广州)有限公司 Synthesis method of hydroxypropyl tetrahydropyrane triol
CN111876452A (en) * 2020-07-01 2020-11-03 江苏瑞蓓丽生物科技有限公司 Method for preparing vitronectin by biological enzyme one-pot method

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