CN115197186B - Preparation method of biomass-based pyranoside derivative - Google Patents

Preparation method of biomass-based pyranoside derivative Download PDF

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CN115197186B
CN115197186B CN202110388743.0A CN202110388743A CN115197186B CN 115197186 B CN115197186 B CN 115197186B CN 202110388743 A CN202110388743 A CN 202110388743A CN 115197186 B CN115197186 B CN 115197186B
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路芳
卢锐
司晓勤
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Zhongke New Catalytic Technology Dalian Co ltd
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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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07—Optical isomers

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Abstract

The invention discloses a preparation method of a biomass-based pyranoside derivative. In particular to a method for preparing a pyranoside derivative by using carbohydrate and glycerol as raw materials and performing multi-step serial connection reaction of selective dehydroxylation and carbon-carbon coupling in deionized water as a solvent under the action of an organometallic complex catalyst and a Lewis acid catalyst. The raw materials used in the method can come from biomass resources completely, the process is simple, the economy is high, and the method has a wide application prospect.

Description

Preparation method of biomass-based pyranoside derivative
Technical Field
The invention relates to the fields of organic synthesis, efficient utilization of biomass resources, fine chemical industry, medicines, daily cosmetics and the like, relates to a preparation method of a biomass-based pyranoside derivative, and in particular relates to a method for obtaining the pyranoside derivative by taking carbohydrate and glycerol as raw materials through continuous multi-step serial reaction.
Background
The C-glycoside has excellent bioactivity, better acid resistance and enzyme catalytic hydrolysis performance, and important application in the industries of organic synthesis, biological medicine and daily cosmetics. However, the methods of C-glycoside synthesis reported in the literature are limited. Among them, US20040048785A1 discloses a method for synthesizing C-glycoside derivatives from xylose and acetylacetone or dibenzoylmethane as raw materials by two-step reaction. The synthesis method of hydroxypropyl tetrahydropyran triol disclosed in CN202010643748.9 is similar to that of US20040048785A1, xylose and acetylacetone are used as raw materials, and the hydroxypropyl tetrahydropyran triol is obtained under the continuous action of alkali and sodium borohydride. CN201910785216.6 discloses a method for preparing hydroxypropyl tetrahydropyran triol (vitriol) by using xylose and ethyl acetoacetate as raw materials and a scandium complex as a catalyst and promoting hydrolysis decarboxylation and carbonyl reduction of ester groups. CN202010629023.4 discloses a method for preparing C-pyranoside, i.e. vitrein, by using a one-pot method of catalyzing the reaction of xylose and isopropanol with biological enzyme. In the process of synthesizing the C-glycoside derivative, acetylacetone, dibenzoylmethane, ethyl acetoacetate and isopropanol are all derived from fossil resources, and 100% biomass-based C-glycoside derivative is difficult to obtain. Therefore, it is important to develop a preparation method of biomass-based C-glycoside derivatives with high efficiency, convenience and high economy.
Disclosure of Invention
The invention aims to provide a preparation method of a biomass-based pyranoside derivative, which specifically uses carbohydrate and glycerol as raw materials, and performs one-pot multi-step serial reaction of selective dehydroxylation and carbon-carbon coupling in deionized water solvent under the action of an organometallic complex catalyst and a Lewis acid catalyst to obtain the pyranoside derivative.
In order to achieve the above purpose, the technical scheme adopted by the invention is as follows:
the specific process method comprises the following steps: the molar ratio was set to 1: 3-3: 1, deionized water solvent (the mass ratio of the carbohydrate raw material to the deionized water solvent is 1:100-2:1), an organic metal complex catalyst (the mol ratio of the organic metal complex catalyst to the carbohydrate raw material is 1:100-1:10), a Lewis acid catalyst (the mol ratio of the anhydrous chloride catalyst to the carbohydrate raw material is 1:200-1:1), and the mass ratio of the molecular sieve catalyst to the carbohydrate raw material is 1:100-1:1) are sequentially added into a stainless steel reaction kettle, the reaction temperature is controlled to be 30-200 ℃, and the reaction time is controlled to be 0.5-24 hours. After the reaction is stopped, the Lewis acid catalyst is removed by filtering the reaction liquid, the organic metal complex catalyst is removed by extracting with ethyl acetate for three times, the water layer is collected, the solvent water is removed by reduced pressure distillation, the light yellow oily liquid is obtained, the light yellow oily liquid is dissolved with absolute ethyl alcohol, the unreacted raw materials are removed by filtering, and the target product C-pyranoside derivative is obtained by reduced pressure distillation and concentration; the embodiment of the invention performs performance evaluation and process condition test in a stainless steel reaction kettle, but is not limited to the stainless steel reaction kettle.
The saccharide carbohydrate is selected from one of glucose, mannose, galactose, xylose, arabinose, lactose, maltose and cellobiose;
the organometallic complex catalyst is at least one selected from 8-hydroxyquinoline molybdenum, 1, 10-phenanthroline dichloro dioxymolybdenum, tetraphenyl porphyrin molybdenum, tetra (p-alkoxyphenyl) porphyrin molybdenum, tetra (p-methylphenyl) porphyrin molybdenum and tetra (p-chlorophenyl) porphyrin molybdenum;
the Lewis acid catalyst is at least one of anhydrous chloride catalyst or molecular sieve catalyst;
the anhydrous chloride catalyst is selected from anhydrous SnCl 4 、TiCl 4 、LaCl 3 、GaCl 3 、AlCl 3 At least one of (a) and (b);
the molecular sieve catalyst is selected from at least one of H beta, sn beta and Zr beta molecular sieves.
Optionally, the lower mass ratio of the carbohydrate to deionized water solvent is selected from the group consisting of 1:100, 1:50, 1:25, 1:20, 1:10, 1:1; the upper limit is selected from 2:1, 3:2, 1:1;
optionally, the lower limit of the molar ratio of the carbohydrate to the glycerol is selected from 1:3, 1:2 and 1:1; the upper limit is selected from 3:1, 3:2, 1:1;
optionally, the lower molar ratio of the organometallic complex catalyst to the saccharide carbohydrate feedstock is selected from the group consisting of 1:100, 1:50, 1:25, 1:20; the upper limit is selected from 1:1, 1:10, 1:20;
optionally, the lower limit of the molar ratio of the anhydrous chloride catalyst to the carbohydrate raw material is selected from 1:200, 1:100 and 1:50; the upper limit is selected from 1:1, 1:20, 1:25, 1:50;
optionally, the lower limit of the mass ratio of the molecular sieve catalyst to the carbohydrate raw material is selected from 1:100, 1:50 and 1:25; the upper limit is selected from 1:1, 1:20, 1:25;
alternatively, the reaction temperature is 150 ℃.
Alternatively, the reaction time is 12 hours.
Compared with the prior art, the method has the following characteristics:
the invention provides a preparation method of a biomass-based pyranoside derivative, which specifically uses carbohydrate and glycerol as raw materials, and under the synergistic effect of an organometallic complex catalyst and a Lewis acid catalyst, the biomass-based pyranoside derivative is obtained by performing selective deoxidation and carbon-carbon coupling multi-step serial reaction in a deionized water solvent. The raw materials can come from biomass resources completely, the process is simple, the solvent is green, the operability is strong, and the method has a large-scale prospect.
Detailed Description
The following examples will aid in the understanding of the present invention, but the present invention is not limited thereto.
The starting materials and catalysts in the examples of the present application were purchased commercially, unless otherwise specified.
Sugar such as glucose and maltose is available from Shanghai Ala Biochemical technology Co.Ltd.
Anhydrous SnCl 4 、LaCl 3 And are available from national drug group chemical company, inc.
Molecular sieves H.beta., zr.beta., sn.beta.and the like are purchased from Tianjin southbound catalyst Co.
The organometallic complex catalyst 8-hydroxyquinoline molybdenum, 1, 10-phenanthroline dichloro dioxymolybdenum, tetraphenyl porphyrin molybdenum, tetra (p-alkoxyphenyl) porphyrin molybdenum, tetra (p-methylphenyl) porphyrin molybdenum, tetra (p-chlorophenyl) porphyrin molybdenum and the like are self-made by a ligand exchange method. Taking a typical preparation process of 1, 10-phenanthroline molybdenum dioxide as an example, dissolving 0.1mol of molybdenum dichloride and 1, 10-phenanthroline in 100mL of tetrahydrofuran respectively, and completely dissolving to prepare two solutions. Adding the tetrahydrofuran solution of molybdenum dichloride dioxide into the tetrahydrofuran solution of 1, 10-phenanthroline while stirring. After the completion of the dropwise addition, the mixed solution was stirred at room temperature for 24 hours. After the stirring was completed, the mixture was filtered and washed to obtain a pale pink solid. And (3) drying at 25 ℃ in vacuum overnight to obtain the 1, 10-phenanthroline dichloro molybdenum dioxygen.
The yield of the product pyranoside derivative is calculated according to the following formula:
example 1
Completely dissolving 1.08kg of glucose in 3.00kg of deionized water, adding into a 20L stainless steel reaction kettle, and stirring for dissolution; 0.36kg of glycerol is dissolved in 3.00kg of deionized water, and the glycerol solution is pumped into a reaction kettle by a peristaltic pump while stirring and uniformly mixed. Adding 0.05kg of transition metal catalyst 1, 10-phenanthroline dichloro molybdenum dioxygen and 0.09kg of Lewis acid catalyst anhydrous LaCl 3 The reaction vessel was closed, stirred, heated to 150℃and reacted for 12 hours. After the reaction was stopped, the solid catalyst was removed by filtration, the organic metal complex catalyst was removed by extraction with ethyl acetate three times (each with an amount of 0.5L), the aqueous layer was collected, the solvent was removed by distillation under reduced pressure to give a pale yellow oily liquid, the unreacted raw material was removed by filtration by dissolution with 1L of absolute ethanol, and the objective C-glucopyranoside derivative was obtained by concentration under reduced pressure in a yield of 33.8% by distillation under 0.45 kg.
Example 2
Completely dissolving 1.08kg of glucose in 3.00kg of deionized water, adding into a 20L stainless steel reaction kettle, and stirring for dissolution; 0.36kg of glycerol is dissolved in 3.00kg of deionized water, and the glycerol solution is pumped into a reaction kettle by a peristaltic pump while stirring and uniformly mixed. Adding 0.05kg of transition metal catalyst 1, 10-phenanthroline dichloro molybdenum dioxygen and 0.10kg of Lewis acid catalyst anhydrous SnCl 4 The reaction vessel was closed, stirred, heated to 150℃and reacted for 12 hours. After the reaction was stopped, the solid catalyst was removed by filtration, the organic metal complex catalyst was removed by extraction with ethyl acetate three times (each with an amount of 0.5L), the aqueous layer was collected, the solvent was removed by distillation under reduced pressure to give a pale yellow oily liquid, the unreacted raw material was removed by filtration by dissolution with 1L of absolute ethanol, and the objective C-glucopyranoside derivative was obtained by concentration under distillation under reduced pressure in a yield of 72.1%.
Example 3
Completely dissolving 1.08kg of glucose in 3.00kg of deionized water, adding into a 20L stainless steel reaction kettle, and stirring for dissolution; 0.36kg of glycerol is dissolved in 3.00kg of deionized water, and the glycerol solution is pumped into a reaction kettle by a peristaltic pump while stirring and uniformly mixed. Adding 0.05kg of transition metal catalyst 1, 10-phenanthroline dichloro molybdenum dioxygen and 0.10kg of Lewis acid catalyst H beta, sealing the reaction kettle, stirring, heating to 150 ℃, and reacting for 12 hours. After the reaction was stopped, the solid catalyst was removed by filtration, the organic metal complex catalyst was removed by extraction with ethyl acetate three times (each with an amount of 0.5L), the aqueous layer was collected, the solvent was removed by distillation under reduced pressure to give a pale yellow oily liquid, which was dissolved with 1L of absolute ethanol, the unreacted starting material was removed by filtration, and the resultant was concentrated by distillation under reduced pressure to give 0.83kg of the objective C-glucopyranoside derivative in 62.3% yield.
Example 4
Completely dissolving 1.08kg of glucose in 3.00kg of deionized water, adding into a 20L stainless steel reaction kettle, and stirring for dissolution; 0.36kg of glycerol is dissolved in 3.00kg of deionized water, and the glycerol solution is pumped into a reaction kettle by a peristaltic pump while stirring and uniformly mixed. Adding 0.05kg of transition metal catalyst 1, 10-phenanthroline dichloro molybdenum dioxygen and 0.10kg of Lewis acid catalyst Zrβ, sealing the reaction kettle, stirring, heating to 150 ℃, and reacting for 12 hours. After the reaction was stopped, the solid catalyst was removed by filtration, the organic metal complex catalyst was removed by extraction with ethyl acetate three times (each with an amount of 0.5L), the aqueous layer was collected, the solvent was removed by distillation under reduced pressure to give a pale yellow oily liquid, the unreacted raw material was removed by filtration by dissolution with 1L of absolute ethanol, and the resultant was concentrated by distillation under reduced pressure to give 1.01kg of the objective C-glucopyranoside derivative in 76.0% yield.
Example 5
Completely dissolving 1.08kg of glucose in 3.00kg of deionized water, adding into a 20L stainless steel reaction kettle, and stirring for dissolution; 0.36kg of glycerol is dissolved in 3.00kg of deionized water, and the glycerol solution is pumped into a reaction kettle by a peristaltic pump while stirring and uniformly mixed. Adding 0.05kg of transition metal catalyst 1, 10-phenanthroline dichloro molybdenum dioxygen and 0.10kg of Lewis acid catalyst Sn beta, sealing the reaction kettle, stirring, heating to 150 ℃, and reacting for 12 hours. After the reaction was stopped, the solid catalyst was removed by filtration, the organic metal complex catalyst was removed by extraction with ethyl acetate three times (each with an amount of 0.5L), the aqueous layer was collected, the solvent was removed by distillation under reduced pressure to give a pale yellow oily liquid, the unreacted raw material was removed by filtration by dissolution with 1L of absolute ethanol, and the objective C-glucopyranoside derivative 1.21kg was obtained by concentration by distillation under reduced pressure in 90.8% yield.
Example 6
Completely dissolving 1.08kg of glucose in 3.00kg of deionized water, adding into a 20L stainless steel reaction kettle, and stirring for dissolution; 0.36kg of glycerol is dissolved in 3.00kg of deionized water, and the glycerol solution is pumped into a reaction kettle by a peristaltic pump while stirring and uniformly mixed. 0.06kg of transition metal catalyst octahydroxyquinoline molybdenum and 0.10kg of Lewis acid catalyst Sn beta are added, the reaction kettle is closed, stirred, heated to 150 ℃ and reacted for 12 hours. After the reaction was stopped, the solid catalyst was removed by filtration, the organic metal complex catalyst was removed by extraction with ethyl acetate three times (each with an amount of 0.5L), the aqueous layer was collected, the solvent was removed by distillation under reduced pressure to give a pale yellow oily liquid, which was dissolved with 1L of absolute ethanol, the unreacted starting material was removed by filtration, and the resultant was concentrated by distillation under reduced pressure to give 0.66kg of the objective C-glucopyranoside derivative in 49.5% yield.
Example 7
2.05kg of maltose is completely dissolved in 3.00kg of deionized water, and is added into a 20L stainless steel reaction kettle to be stirred and dissolved; 0.36kg of glycerol is dissolved in 3.00kg of deionized water, and the glycerol solution is pumped into a reaction kettle by a peristaltic pump while stirring and uniformly mixed. Adding 0.05kg of transition metal catalyst 1, 10-phenanthroline dichloro molybdenum dioxygen and 0.23kg of Lewis acid catalyst Sn beta, sealing the reaction kettle, stirring, heating to 150 ℃, and reacting for 12 hours. After the reaction was stopped, the solid catalyst was removed by filtration, the organic metal complex catalyst was removed by extraction with ethyl acetate three times (each with an amount of 0.5L), the aqueous layer was collected, the solvent was removed by distillation under reduced pressure to give a pale yellow oily liquid, which was dissolved with 1L of absolute ethanol, the unreacted starting material was removed by filtration, and the resultant was concentrated by distillation under reduced pressure to give 1.90kg of the objective C-maltopyranoside derivative in 82.5% yield.
In summary, the application provides a preparation method of a full biomass-based pyranoside derivative, which takes carbohydrate and glycerol as raw materials, and performs one-pot multi-step serial reaction in deionized water solvent under the synergistic effect of an organometallic complex catalyst and a Lewis acid catalyst to obtain the pyranoside derivative. The raw materials can come from biomass resources completely, the process is simple and green, the operability is strong, and the method has a large-scale prospect.
The foregoing description is only a few examples of the present application and is not intended to limit the present application in any way, and although the present application is disclosed in the preferred examples, it is not intended to limit the present application, and any person skilled in the art may make some changes or modifications to the disclosed technology without departing from the scope of the technical solution of the present application, and the technical solution is equivalent to the equivalent embodiments.

Claims (11)

1. A preparation method of biomass-based pyranoside derivative is characterized in that,
at least comprises the following steps: taking a mixture containing carbohydrate and glycerol as a raw material, and under the action of an organometallic complex catalyst and a Lewis acid catalyst, performing multi-step serial reaction of selective dehydroxylation and carbon-carbon coupling in a solvent to obtain a biomass-based pyranoside derivative;
the saccharide carbohydrate is selected from one of glucose, mannose, galactose, xylose and arabinose;
the organometallic complex catalyst is at least one of 8-hydroxyquinoline molybdenum and 1, 10-phenanthroline dichloro molybdenum dioxide;
the Lewis acid catalyst is at least one of anhydrous chloride catalyst or molecular sieve catalyst;
the anhydrous chloride catalyst is selected from anhydrous SnCl 4 、LaCl 3 At least one of (a) and (b);
the molecular sieve catalyst is at least one selected from H beta, sn beta and Zr beta molecular sieves;
the solvent is deionized water.
2. The method according to claim 1, wherein,
at least comprises the following steps: adding carbohydrate into deionized water, stirring for dissolving, adding glycerol by a peristaltic pump, adding an organic metal complex catalyst and a Lewis acid catalyst, and heating for reaction;
filtering after the reaction is finished, extracting by ethyl acetate, collecting a water layer, dissolving by absolute ethyl alcohol after reduced pressure distillation, filtering and then carrying out reduced pressure distillation to obtain the biomass-based pyranoside derivative.
3. The method according to claim 1, wherein,
the mass ratio of the carbohydrate to the deionized water solvent is 1: 100-2: 1.
4. the method according to claim 1, wherein,
the molar ratio of the carbohydrate to the glycerol is 1:3~3:1.
5. the method according to claim 1, wherein,
the molar ratio of the using amount of the organometallic complex catalyst to the carbohydrate raw material of the saccharide is 1: 100-1: 10.
6. the method according to claim 1, wherein,
the molar ratio of the dosage of the anhydrous chloride catalyst to the carbohydrate raw material of the sugar is 1: 200-1: 1.
7. the method according to claim 1, wherein,
the mass ratio of the dosage of the molecular sieve catalyst to the carbohydrate raw material of the sugar is 1: 100-1: 1.
8. the method according to claim 1, wherein,
the reaction temperature is 30-200 ℃.
9. The method according to claim 1, wherein,
the reaction temperature was 150 ℃.
10. The method according to claim 1, wherein,
the reaction time is 0.5-24 hours.
11. The method according to claim 1, wherein,
the reaction time was 12 hours.
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