CN115197186A - Preparation method of biomass-based pyranoside derivative - Google Patents

Preparation method of biomass-based pyranoside derivative Download PDF

Info

Publication number
CN115197186A
CN115197186A CN202110388743.0A CN202110388743A CN115197186A CN 115197186 A CN115197186 A CN 115197186A CN 202110388743 A CN202110388743 A CN 202110388743A CN 115197186 A CN115197186 A CN 115197186A
Authority
CN
China
Prior art keywords
catalyst
carbohydrate
molybdenum
reaction
biomass
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CN202110388743.0A
Other languages
Chinese (zh)
Other versions
CN115197186B (en
Inventor
路芳
卢锐
司晓勤
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Zhongke New Catalytic Technology Dalian Co ltd
Original Assignee
Dalian Institute of Chemical Physics of CAS
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Dalian Institute of Chemical Physics of CAS filed Critical Dalian Institute of Chemical Physics of CAS
Priority to CN202110388743.0A priority Critical patent/CN115197186B/en
Publication of CN115197186A publication Critical patent/CN115197186A/en
Application granted granted Critical
Publication of CN115197186B publication Critical patent/CN115197186B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Saccharide Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

The invention discloses a preparation method of a biomass-based pyranoside derivative. In particular to a method for obtaining pyranoside derivatives by taking carbohydrate and glycerol as raw materials and carrying out multi-step series reaction of selective dehydroxylation and carbon-carbon coupling in solvent deionized water under the action of an organic metal complex catalyst and a Lewis acid catalyst. The raw materials used in the method can be completely derived from biomass resources, and the method is simple in process, high in economy and wide in 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 engineering, medicines, daily cosmetics and the like, relates to a preparation method of a biomass-based pyranoside derivative, and particularly relates to a method for obtaining the pyranoside derivative by taking carbohydrate and glycerol as raw materials through continuous multi-step tandem reaction.
Background
The C-glucoside has excellent biological activity, better acid-resistant and enzyme-catalyzed hydrolysis performance, and important application in organic synthesis, biomedicine and daily cosmetic industries. However, the methods of C-glycoside synthesis reported in the literature are limited. Wherein, US20040048785A1 discloses a method for synthesizing C-glycoside derivatives by taking xylose and acetylacetone or dibenzoylmethane as raw materials through two-step reaction. CN202010643748.9 discloses a synthesis method of hydroxypropyl tetrahydropyrane triol, which is similar to that of US20040048785A1, and xylose and acetylacetone are used as raw materials to obtain the hydroxypropyl tetrahydropyrane triol under the continuous action of alkali and sodium borohydride. CN201910785216.6 discloses a method for preparing a product hydroxypropyl tetrahydropyrane triol (vitriol) by using xylose and ethyl acetoacetate as raw materials and a metal scandium complex as a catalyst and promoting hydrolysis decarboxylation of an ester group and carbonyl reduction. CN202010629023.4 discloses a method for preparing C-pyranoside, namely vitreoside, by using a one-pot method of reaction of xylose and isopropanol catalyzed by a biological enzyme. In the above process for synthesizing the C-glycoside derivative, the acetylacetone, dibenzoylmethane, ethyl acetoacetate, and isopropyl alcohol used are derived from fossil resources, and it is difficult to obtain 100% biomass-based C-glycoside derivatives. Therefore, it is very important to develop a preparation method of biomass-based C-glucoside derivatives with high efficiency, convenience and high economy.
Disclosure of Invention
The invention aims to provide a preparation method of biomass-based pyranoside derivatives, which specifically comprises the step of carrying out one-pot multi-step series reaction of selective dehydroxylation and carbon-carbon coupling in a deionized water solvent by taking carbohydrate and glycerol as raw materials under the action of an organic metal complex catalyst and a Lewis acid catalyst to obtain the pyranoside derivatives.
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 the components in a molar ratio of 1:3 to 3: the method comprises the following steps of 1, sequentially adding a saccharide carbohydrate and glycerol reaction raw material, a deionized water solvent (the mass ratio of the saccharide carbohydrate raw material to the deionized water solvent is 1. After the reaction is stopped, filtering reaction liquid to remove a Lewis acid catalyst, extracting with ethyl acetate for three times to remove an organic metal complex catalyst, collecting a water layer, distilling under reduced pressure to remove solvent water to obtain light yellow oily liquid, dissolving with absolute ethyl alcohol, filtering to remove unreacted raw materials, and distilling and concentrating under reduced pressure to obtain a target product C-pyranoside derivative; 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 organic metal complex catalyst is selected from at least one of 8-hydroxyquinoline molybdenum, 1, 10-phenanthroline dichloro-dioxy-molybdenum, tetraphenyl porphyrin molybdenum, tetra (p-alkoxy phenyl) porphyrin molybdenum, tetra (p-methylphenyl) porphyrin molybdenum and tetra (p-chlorophenyl) porphyrin molybdenum;
the Lewis acid catalyst is at least one of an anhydrous chloride catalyst or a 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;
the molecular sieve catalyst is at least one of H beta, sn beta and Zr beta molecular sieves.
Optionally, the lower limit of the mass ratio of the carbohydrate to the deionized water solvent is selected from 1; the upper limit is selected from 2;
optionally, the lower limit of the molar ratio of carbohydrate to glycerol is selected from 1; the upper limit is selected from 3;
optionally, the lower limit of the molar ratio of the amount of the organometallic complex catalyst to the saccharide carbohydrate raw material is selected from the group consisting of 1; the upper limit is selected from 1,10, 1;
optionally, the lower limit of the molar ratio of the anhydrous chloride catalyst to the carbohydrate raw material is selected from 1; the upper limit is selected from 1, 1;
optionally, the lower limit of the mass ratio of the amount of the molecular sieve catalyst to the carbohydrate feedstock is selected from 1; the upper limit is selected from 1, 1;
optionally, the reaction temperature is 150 ℃.
Optionally, the reaction time is 12 hours.
Compared with the route of the prior art, the method has the following characteristics:
the invention provides a preparation method of a biomass-based pyranoside derivative, which specifically comprises the steps of taking carbohydrate and glycerol as raw materials, and carrying out selective deoxidation and carbon-carbon coupling multistep series reaction in a deionized water solvent under the synergistic action of an organic metal complex catalyst and a Lewis acid catalyst to obtain the pyranoside derivative. The raw materials can be completely derived from biomass resources, 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 invention, but the summary of the invention is not limited thereto.
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, inc.
Anhydrous SnCl 4 、LaCl 3 And the like are purchased from chemical agents of the national drug group, ltd.
Molecular sieves, hbeta, zr beta, sn beta, etc., were purchased from tianjin south chemical catalyst, inc.
The organometallic complex catalyst is prepared by ligand exchange method from 8-hydroxyquinoline molybdenum, 1, 10-phenanthroline dichloro-molybdenum dioxide, tetraphenyl porphyrin molybdenum, tetra (p-alkoxy phenyl) porphyrin molybdenum, tetra (p-methylphenyl) porphyrin molybdenum, tetra (p-chlorophenyl) porphyrin molybdenum and the like. Taking a typical preparation process of 1, 10-phenanthroline dimolybdenum as an example, 0.1mol of molybdenum dichloride and 1, 10-phenanthroline are dissolved in 100mL of tetrahydrofuran respectively and are completely dissolved to prepare two parts of solution. Adding the tetrahydrofuran solution of molybdenum oxydichloride into the tetrahydrofuran solution of 1, 10-phenanthroline while stirring. After the addition, the mixed solution was stirred at room temperature for 24 hours. After stirring, filtering and washing to obtain a light pink solid. Vacuum drying at 25 deg.C overnight to obtain 1, 10-phenanthroline dichloro molybdenum.
The yield of the pyranoside derivative was calculated according to the following formula:
Figure BDA0003016064330000041
example 1
Figure BDA0003016064330000042
Completely dissolving 1.08kg of glucose in 3.00kg of deionized water, adding into a 20L stainless steel reaction kettle, and stirring for dissolving; dissolving 0.36kg of glycerol in 3.00kg of deionized water, pumping the glycerol solution into a reaction kettle by using a peristaltic pump while stirring, and uniformly mixing. Adding 0.05kg of transition metal catalyst 1, 10-phenanthroline dichloro-molybdenum and 0.09kg of Lewis acid catalyst anhydrous LaCl 3 And sealing the reaction kettle, stirring, heating to 150 ℃, and reacting for 12 hours. After the reaction is stopped, the reaction liquid is filtered to remove the solid catalyst, ethyl acetate is extracted for three times (each dosage is 0.5L) to remove the organic metal complex catalyst, a water layer is collected, the solvent is removed by reduced pressure distillation to obtain light yellow oily liquid, the light yellow oily liquid is dissolved by 1L of absolute ethyl alcohol, unreacted raw materials are removed by filtration, the reduced pressure distillation and concentration are carried out to obtain 0.45kg of the target product C-glucopyranoside derivative, and the yield is 33.8%.
Example 2
Figure BDA0003016064330000043
Completely dissolving 1.08kg of glucose in 3.00kg of deionized water, adding the solution into a 20L stainless steel reaction kettle, and stirring and dissolving; dissolving 0.36kg of glycerol in 3.00kg of deionized water, and pumping the glycerol solution into a reaction kettle by using a peristaltic pump while stirringAnd (4) uniformly mixing. Adding 0.05kg of transition metal catalyst 1, 10-phenanthroline dichloro-molybdenum and 0.10kg of Lewis acid catalyst anhydrous SnCl 4 And sealing the reaction kettle, stirring, heating to 150 ℃, and reacting for 12 hours. After the reaction is stopped, the reaction liquid is filtered to remove the solid catalyst, ethyl acetate is extracted for three times (each dosage is 0.5L) to remove the organic metal complex catalyst, a water layer is collected, the solvent is removed by reduced pressure distillation to obtain light yellow oily liquid, the light yellow oily liquid is dissolved by 1L of absolute ethyl alcohol, unreacted raw materials are removed by filtration, the reduced pressure distillation and concentration are carried out to obtain 0.96kg of the target product C-glucopyranoside derivative, and the yield is 72.1%.
Example 3
Figure BDA0003016064330000051
Completely dissolving 1.08kg of glucose in 3.00kg of deionized water, adding into a 20L stainless steel reaction kettle, and stirring for dissolving; dissolving 0.36kg of glycerol in 3.00kg of deionized water, pumping the glycerol solution into a reaction kettle by using a peristaltic pump while stirring, and uniformly mixing. Adding 0.05kg of transition metal catalyst 1, 10-phenanthroline dichloro molybdenum 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 is stopped, the reaction liquid is filtered to remove the solid catalyst, ethyl acetate is extracted for three times (each dosage is 0.5L) to remove the organic metal complex catalyst, a water layer is collected, the solvent is removed by reduced pressure distillation to obtain light yellow oily liquid, the light yellow oily liquid is dissolved by 1L of absolute ethyl alcohol, unreacted raw materials are removed by filtration, the reduced pressure distillation and concentration are carried out to obtain 0.83kg of the target product C-glucopyranoside derivative, and the yield is 62.3%.
Example 4
Figure BDA0003016064330000052
Completely dissolving 1.08kg of glucose in 3.00kg of deionized water, adding the solution into a 20L stainless steel reaction kettle, and stirring and dissolving; dissolving 0.36kg of glycerol in 3.00kg of deionized water, pumping the glycerol solution into a reaction kettle by using a peristaltic pump while stirring, and uniformly mixing. Adding 0.05kg of 1, 10-phenanthroline dichloro molybdenum oxide serving as a transition metal catalyst and 0.10kg of Zr beta serving as a Lewis acid catalyst, sealing the reaction kettle, stirring, heating to 150 ℃, and reacting for 12 hours. After the reaction is stopped, the reaction liquid is filtered to remove the solid catalyst, ethyl acetate is extracted for three times (each dosage is 0.5L) to remove the organic metal complex catalyst, a water layer is collected, the solvent is removed by reduced pressure distillation to obtain light yellow oily liquid, the light yellow oily liquid is dissolved by 1L of absolute ethyl alcohol, unreacted raw materials are removed by filtration, the reduced pressure distillation and concentration are carried out to obtain 1.01kg of the target product C-glucopyranoside derivative, and the yield is 76.0%.
Example 5
Figure BDA0003016064330000061
Completely dissolving 1.08kg of glucose in 3.00kg of deionized water, adding into a 20L stainless steel reaction kettle, and stirring for dissolving; dissolving 0.36kg of glycerol in 3.00kg of deionized water, pumping the glycerol solution into a reaction kettle by using a peristaltic pump while stirring, and uniformly mixing. Adding 0.05kg of transition metal catalyst 1, 10-phenanthroline dichloro molybdenum 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 is stopped, filtering the reaction liquid to remove the solid catalyst, extracting with ethyl acetate for three times (0.5L for each dosage) to remove the organic metal complex catalyst, collecting a water layer, distilling under reduced pressure to remove the solvent to obtain a light yellow oily liquid, dissolving with 1L of absolute ethyl alcohol, filtering to remove unreacted raw materials, distilling under reduced pressure and concentrating to obtain 1.21kg of the target product C-glucopyranoside derivative, wherein the yield is 90.8%.
Example 6
Figure BDA0003016064330000062
Completely dissolving 1.08kg of glucose in 3.00kg of deionized water, adding the solution into a 20L stainless steel reaction kettle, and stirring and dissolving; dissolving 0.36kg of glycerol in 3.00kg of deionized water, pumping the glycerol solution into a reaction kettle by using a peristaltic pump while stirring, and uniformly mixing. Adding 0.06kg of transition metal catalyst octohydroxyquinoline molybdenum 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 is stopped, the reaction liquid is filtered to remove the solid catalyst, ethyl acetate is extracted for three times (each dosage is 0.5L) to remove the organic metal complex catalyst, a water layer is collected, the solvent is removed by reduced pressure distillation to obtain light yellow oily liquid, the light yellow oily liquid is dissolved by 1L of absolute ethyl alcohol, unreacted raw materials are removed by filtration, the reduced pressure distillation and concentration are carried out to obtain 0.66kg of the target product C-glucopyranoside derivative, and the yield is 49.5%.
Example 7
Figure BDA0003016064330000071
Completely dissolving 2.05kg of maltose in 3.00kg of deionized water, adding the solution into a 20L stainless steel reaction kettle, and stirring and dissolving; dissolving 0.36kg of glycerol in 3.00kg of deionized water, pumping the glycerol solution into a reaction kettle by using a peristaltic pump while stirring, and uniformly mixing. Adding 0.05kg of transition metal catalyst 1, 10-phenanthroline dichloro molybdenum 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 is stopped, the reaction liquid is filtered to remove the solid catalyst, ethyl acetate is extracted for three times (each dosage is 0.5L) to remove the organic metal complex catalyst, a water layer is collected, the solvent is removed by reduced pressure distillation to obtain light yellow oily liquid, the light yellow oily liquid is dissolved by 1L of absolute ethyl alcohol, unreacted raw materials are removed by filtration, the reduced pressure distillation and concentration are carried out to obtain 1.90kg of the target product C-maltopyranoside derivative, and the yield is 82.5%.
In summary, the application provides a preparation method of a full biomass-based pyranoside derivative, which takes carbohydrate and glycerol as raw materials, and carries out one-pot multi-step series reaction in a deionized water solvent under the synergistic action of an organic metal complex catalyst and a Lewis acid catalyst to obtain the pyranoside derivative. The raw materials can be completely from biomass resources, the process is simple and green, the operability is strong, and the method has a large-scale prospect.
Although the present application has been described with reference to a few embodiments, it should be understood that various changes, substitutions and alterations can be made herein without departing from the spirit and scope of the application as defined by the appended claims.

Claims (10)

1. A preparation method of biomass-based pyranoside derivatives is characterized by at least comprising the following steps: the biomass-based pyranoside derivative is obtained by taking a mixture containing carbohydrate and glycerol as a raw material and performing multi-step series reaction of selective dehydroxylation and carbon-carbon coupling in a solvent under the action of an organic metal complex catalyst and a Lewis acid catalyst.
2. The method of claim 1, wherein:
the carbohydrate is selected from one of glucose, mannose, galactose, xylose, arabinose, lactose, maltose and cellobiose;
the organic metal complex catalyst is selected from at least one of 8-hydroxyquinoline molybdenum, 1, 10-phenanthroline dichloro-dioxy-molybdenum, tetraphenyl porphyrin molybdenum, tetra (p-alkoxy phenyl) porphyrin molybdenum, tetra (p-methylphenyl) porphyrin molybdenum and tetra (p-chlorophenyl) porphyrin molybdenum;
the Lewis acid catalyst is at least one of an anhydrous chloride catalyst or a 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);
the molecular sieve catalyst is at least one of H beta, sn beta and Zr beta molecular sieves;
the solvent is deionized water.
3. The production method according to claim 1, characterized in that: at least comprises the following steps: adding carbohydrate into deionized water, stirring for dissolving, simultaneously adding glycerol by using a peristaltic pump, adding an organic metal complex catalyst and a Lewis acid catalyst, and heating for reaction;
and after the reaction is finished, filtering, extracting with ethyl acetate, collecting a water layer, dissolving with absolute ethyl alcohol after reduced pressure distillation, filtering, and then carrying out reduced pressure distillation to obtain the biomass-based pyranoside derivative.
4. The production method according to claim 2, characterized in that: the mass ratio of the carbohydrate to the deionized water solvent is 1:100 to 2:1.
5. the method of claim 1, wherein: the molar ratio of the carbohydrate to the glycerol is 1:3 to 3:1.
6. the production method according to claim 1, characterized in that: the molar ratio of the dosage of the organic metal complex catalyst to the carbohydrate raw material is 1:100 to 1:10.
7. the production method according to claim 2, characterized in that: the molar ratio of the consumption of the anhydrous chloride catalyst to the carbohydrate raw material is 1: 200-1: 1.
8. the method of claim 2, wherein: the mass ratio of the dosage of the molecular sieve catalyst to the carbohydrate raw material is 1:100 to 1:1.
9. the method of claim 1, wherein: the reaction temperature is 30-200 ℃;
preferably 150 deg.c.
10. The method of claim 1, wherein: the reaction time is 0.5 to 24 hours;
preferably 12 hours.
CN202110388743.0A 2021-04-12 2021-04-12 Preparation method of biomass-based pyranoside derivative Active CN115197186B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN202110388743.0A CN115197186B (en) 2021-04-12 2021-04-12 Preparation method of biomass-based pyranoside derivative

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN202110388743.0A CN115197186B (en) 2021-04-12 2021-04-12 Preparation method of biomass-based pyranoside derivative

Publications (2)

Publication Number Publication Date
CN115197186A true CN115197186A (en) 2022-10-18
CN115197186B CN115197186B (en) 2024-04-16

Family

ID=83571605

Family Applications (1)

Application Number Title Priority Date Filing Date
CN202110388743.0A Active CN115197186B (en) 2021-04-12 2021-04-12 Preparation method of biomass-based pyranoside derivative

Country Status (1)

Country Link
CN (1) CN115197186B (en)

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20040048785A1 (en) * 2000-12-22 2004-03-11 Societe L'oreal S.A. C-glycoside compounds for stimulating the synthesis of glycosaminoglycans
CN101125837A (en) * 2007-09-30 2008-02-20 华东理工大学 C-glycosides type slycolipid compounds and use thereof
US20080171706A1 (en) * 2004-03-23 2008-07-17 Vlaams Interuniversitair Instituut Voor Biotechnologie Vzw Anti-Adhesive Compounds to Prevent and Treat Bacterial Infections
CN103124727A (en) * 2010-07-20 2013-05-29 百时美施贵宝公司 Substituted 3-phenyl-1,2,4-oxadiazole compounds
CN110467591A (en) * 2019-08-23 2019-11-19 上海克琴科技有限公司 Rare earth metal complex promote one pot process cosmetic active object Bose because

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20040048785A1 (en) * 2000-12-22 2004-03-11 Societe L'oreal S.A. C-glycoside compounds for stimulating the synthesis of glycosaminoglycans
US20080171706A1 (en) * 2004-03-23 2008-07-17 Vlaams Interuniversitair Instituut Voor Biotechnologie Vzw Anti-Adhesive Compounds to Prevent and Treat Bacterial Infections
CN101125837A (en) * 2007-09-30 2008-02-20 华东理工大学 C-glycosides type slycolipid compounds and use thereof
CN103124727A (en) * 2010-07-20 2013-05-29 百时美施贵宝公司 Substituted 3-phenyl-1,2,4-oxadiazole compounds
CN110467591A (en) * 2019-08-23 2019-11-19 上海克琴科技有限公司 Rare earth metal complex promote one pot process cosmetic active object Bose because

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
YOU YANG等: ""Recent Advances in the Chemical Synthesis of C‑Glycosides"", 《CHEMICAL REVIEWS》, vol. 117, pages 12281 - 12356, XP055807371, DOI: 10.1021/acs.chemrev.7b00234 *
廖进喜等: ""过渡金属催化的偶联反应在合成C-糖苷中的应用"", 《有机化学》, vol. 37, pages 1382 - 1391 *

Also Published As

Publication number Publication date
CN115197186B (en) 2024-04-16

Similar Documents

Publication Publication Date Title
CN110590819B (en) Process for producing organoboron compound and process for producing beta-hydroxyorganoboron compound
CN113563370A (en) Preparation method for preparing beta-boryl ketone with substituent at alpha position by catalyzing chitosan loaded copper material
CN111039980A (en) Cuprous complex containing diphosphine o-carborane ligand and preparation and application thereof
CN113372227A (en) Synthesis process of high-purity benzethonium chloride
CN111229264A (en) Method for preparing 5-hydroxymethylfurfural, catalyst thereof and preparation method of catalyst
CN115197186B (en) Preparation method of biomass-based pyranoside derivative
CN105964306A (en) Poly(ionic liquid)-based magnetic nanoparticle and its preparation method and use in three-ingredient reaction
CN1060913C (en) Larva of snout moth killing tablets and production thereof
CN115181081B (en) Synthesis method of beta-phenyl-gamma-butyrolactone
CN115197185B (en) Preparation method of transition metal catalyzed pyranoside derivative
CN112322676B (en) Method for preparing fluvastatin by enzyme catalysis
CN111499538B (en) Preparation method of (2S, 3R) -2-acylaminomethyl-3-hydroxybutyrate
CN110655497B (en) Method for preparing gamma-valerolactone by organic-metal catalyst one-pot method
CN110002939B (en) Efficient adamantane synthesis method
CN109824629A (en) A method of 3- amino -5-(alpha-amido ethyl is prepared using N- acetyl-D-Glucose) tetrahydrofuran
CN116715645A (en) Synthesis and purification method of hydroxypropyl tetrahydropyran triol
CN115197282A (en) Preparation method of pyranoside derivative
CN114437142B (en) Preparation method of crotyl palladium chloride dimer
CN1226260C (en) Method for synthesizing deca-isoprene alcohol
CN115772077B (en) Method for preparing chiral D-glyceric acid by catalytic conversion of arabitol
CN114478446B (en) Method for preparing chromogen III by converting D-acetamido glucose
CN114797988B (en) Synthesis of composite catalyst and method for preparing beta-isophorone
CN110372510B (en) Method for catalytically synthesizing aryl acetate derivative by utilizing surface modified sludge carbon
CN102731582B (en) Preparation method of acetyl halogenated saccharide
CN117327037A (en) Method for preparing nitrogen-containing heterocyclic compound 3-acetamido-5-acetyl furan

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
TA01 Transfer of patent application right

Effective date of registration: 20230823

Address after: 116000 Xingang Village, Changxing Island Economic Zone, Dalian City, Liaoning Province

Applicant after: Zhongke New Catalytic Technology (Dalian) Co.,Ltd.

Address before: 116023 No. 457, Zhongshan Road, Liaoning, Dalian

Applicant before: DALIAN INSTITUTE OF CHEMICAL PHYSICS, CHINESE ACADEMY OF SCIENCES

TA01 Transfer of patent application right
GR01 Patent grant
GR01 Patent grant