CN101875675A - Preparation method of some glucoside - Google Patents
Preparation method of some glucoside Download PDFInfo
- Publication number
- CN101875675A CN101875675A CN2010101972445A CN201010197244A CN101875675A CN 101875675 A CN101875675 A CN 101875675A CN 2010101972445 A CN2010101972445 A CN 2010101972445A CN 201010197244 A CN201010197244 A CN 201010197244A CN 101875675 A CN101875675 A CN 101875675A
- Authority
- CN
- China
- Prior art keywords
- washing
- stirring
- water
- alpha
- brominated
- 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.)
- Pending
Links
Landscapes
- Saccharide Compounds (AREA)
Abstract
The invention provides a preparation method of some glucoside, comprising the following steps: dissolving glucose in anhydrous pyridine, adding acetic anhydride, stirring for 5 hours at a room temperature, adding a small amount of ice water, stirring and then diluting with chloroform; drying ethanol as a solvent by distillation, washing and then dissolving in CH2C12; carrying out ice bath at 0 DEG C, stirring for 10 minutes, dropwise adding 33% of hydrobromic acid glacial acetic acid solution, stirring for 5 hours at the room temperature, and then removing the solvent by distillation; diluting and pouring dichloromethane into ice water, washing with saturated NaHCO3 and NaCl, drying by distillation, and then washing with ethanol and diethyl ether to obtain alpha-bromo-2,3,4,6-4-O-acetyl glucopyranose; and placing 4-hydroxy benzaldehyde, sodium hydroxide, tetrabutyl amonium bromide, water and trichloromethane in a three-necked flask, stirring and dissolving at 50 DEG C, dropwise adding trichloromethane solution containing bromo-acetyl glucose (20mmol) to react for 6 hours, respectively washing with 1M NaOH and water for twice, drying, and finally carrying out silicagel column chromatography to obtain 4-formoxyl phenyl-2,3,4,6-4-O-acetyl-beta-D-glucopyranoside.
Description
Technical field
The invention discloses the preparation method of some glucoside.
Background technology
Glucosides, English name: glycoside; Glucoside also claims glycoside.Be dehydrations such as the hemiacetal hydroxyl of monose or oligosaccharides and hydroxyl, amino or the thiol in another molecule and produce hydrate.Therefore a glucosides can be divided into two portions.A part is the residue (sugar removes the hemiacetal hydroxyl) of sugar, and another part is aglucon (an aglucone branch), and the aglucon part can be very simple, also can be very complicated.Glucosides is distributed widely in root, stem, leaf, flower and the fruit of plant.Be band look crystal mostly, can be water-soluble.General bitter.Some has severe toxicity.Generate sugar and other materials during hydrolysis.For example the final product of amygdaloside (amygdalin) C20H27NO11 hydrolysis is glucose C6H12O6, phenyl aldehyde C6H5CHO and prussic acid HCN.The glucosides useful as drug.A lot of Effective Components of Chinese Herb are exactly glucosides, for example radix bupleuri, balloonflower root, polygala root etc.Because the difference of steric configuration, glucosides has α and β two types.The glycosides of glucose (heteroside) and other sugared glycosides, great majority are β-type glucosides.
Summary of the invention
The preparation method of some glucoside, its preparation scheme:
I: get glucose 5g and be dissolved in the 20mL anhydrous pyridine, be stirred to fully dissolving after, add diacetyl oxide 25mL, stirring at room 5h, the back adds a small amount of frozen water and stirs 10min, again with the dilution of 50mL chloroform.Separate organic phase, wash with water successively, 2M sulfuric acid, saturated aqueous sodium carbonate, the saturated sodium-chloride water solution washing, anhydrous sodium sulfate drying, the evaporated under reduced pressure solvent gets colorless transparent syrup.The back gets white solid with 95% washing with alcohol, heavy 9.86g, productive rate 91%.
II: get the full acetylated glucose of 5g (product among the I), be dissolved in 20mLCH
2Cl
2In, behind 0 ℃ of stirring of ice bath 10min, slowly drip 33% Hydrogen bromide glacial acetic acid solution 12mL.Change stirring at room 5h after adding into.After decompression steams partial solvent, add the dilution of 50mL methylene dichloride, pour in the 100mL frozen water.Separate organic phase, wash saturated NaHCO successively with water
3, saturated NaCl washing, the evaporated under reduced pressure solvent gets pale brown sugar colour slurry.The back with 95% ethanol and a small amount of ether wash the white solid powder, alpha-brominated-2,3,4,6-four-O-ethanoyl Glucopyranose, weight 3.54g, productive rate 67%, mp.87-89 ℃ (lit.88-89 ℃)
[43]
With step preparation, alpha-brominated-2,3,4; 6-four-O-ethanoyl galactopyranose, mp.74-76 ℃, alpha-brominated-2 ', 3 '; 4 ', 6 ', 2,4; 6-seven-O-ethanoyl pyrans lactose, mp.122-124 ℃, alpha-brominated-2,3; 4,6-four-O-benzoyl xylopyranose, mp.135-137 ℃, alpha-brominated-2; 3,4,6-four-O-benzoyl ribopyranose, mp.121-122 ℃.
III: disubstituted-4-hydroxy phenyl aldehyde 2.44g (20mmol), sodium hydroxide 0.84g (21mmol), Tetrabutyl amonium bromide 0.64g (2mmol), water 10ml, trichloromethane 10mL contains in the 100mL there-necked flask, and 50 ℃ are stirred to dissolving fully, and the back slowly drips the chloroform soln 25mL that contains bromo acetyl glucosamine 8.22g (20mmol), continue reaction 6h, TLC tracks to and reacts completely.Separate organic phase, 1MNaOH washing, washing each 2 times, anhydrous magnesium sulfate drying, evaporated under reduced pressure solvent; obtain 4-formyl radical phenyl-2,3,4 through silica gel column chromatography, 6-four-O-ethanoyl-β-D-glucopyranoside; white solid, heavy 4.55g, productive rate 50%, mp.142-143 ℃.Foregoing invention belongs to productive rate height, preferred version easy and simple to handle.
Description of drawings
This invents no accompanying drawing.
Embodiment
The following stated embodiment understands the present invention in detail.Go out outside the other explanation, all marks and per-cent are all calculated by weight.
Embodiment 1
Get glucose 5g and be dissolved in the 20mL anhydrous pyridine, be stirred to fully dissolving after, add diacetyl oxide 25mL, stirring at room 5h, the back adds a small amount of frozen water and stirs 10min, again with the dilution of 50mL chloroform.Separate organic phase, wash with water successively, 2M sulfuric acid, saturated aqueous sodium carbonate, the saturated sodium-chloride water solution washing, anhydrous sodium sulfate drying gets white solid with 95% washing with alcohol after the evaporated under reduced pressure, heavy 9.86g, productive rate 91%.Gains are: acetyl glucose.
Embodiment 2
Get the full acetylated glucose of 5g (product among the I), be dissolved in 20mL CH
2Cl
2In, behind 0 ℃ of stirring of ice bath 10min, slowly drip 33% Hydrogen bromide glacial acetic acid solution 12mL.Change stirring at room 5h after adding into.After decompression steams partial solvent, add the dilution of 50mL methylene dichloride, pour in the 100mL frozen water.Separate organic phase, wash saturated NaHCO successively with water
3, saturated NaCl washing, after the evaporated under reduced pressure with 95% ethanol and a small amount of ether wash the white solid powder, alpha-brominated-2,3,4,6-four-O-ethanoyl Glucopyranose, weight 3.54g, productive rate 67%, mp.87-89 ℃ (lit.88-89 ℃)
[43]
Embodiment 3
Disubstituted-4-hydroxy phenyl aldehyde 2.44g (20mmol), sodium hydroxide 0.84g (21mmol), Tetrabutyl amonium bromide 0.64g (2mmol), water 10ml, trichloromethane 10mL contains in the 100mL there-necked flask, and 50 ℃ are stirred to dissolving fully, and the back slowly drips the chloroform soln 25mL that contains bromo acetyl glucosamine 8.22g (20mmol), continue reaction 6h, TLC tracks to and reacts completely.Separate organic phase, the 1MNaOH washing, washing each 2 times, anhydrous magnesium sulfate drying, the evaporated under reduced pressure solvent obtains 4-formyl radical phenyl-2,3,4 through silica gel column chromatography, 6-four-O-ethanoyl-β-D-glucopyranoside.
Claims (2)
1. the preparation method of some glucoside, its preparation scheme:
I: get glucose 5g and be dissolved in the 20mL anhydrous pyridine, be stirred to fully dissolving after, add diacetyl oxide 25mL, stirring at room 5h adds a small amount of frozen water and stirs 10min, again with the dilution of 50mL chloroform; Separate organic phase, wash with water successively, 2M sulfuric acid, saturated aqueous sodium carbonate, the saturated sodium-chloride water solution washing, anhydrous sodium sulfate drying, the evaporated under reduced pressure solvent gets colorless transparent syrup; The back gets white solid with 95% washing with alcohol, heavy 9.86g, productive rate 91%;
II: get the full acetylated glucose of 5g---product among the I, be dissolved in 20mL CH
2Cl
2In, behind 0 ℃ of stirring of ice bath 10min, slowly drip 33% Hydrogen bromide glacial acetic acid solution 12mL; Change stirring at room 5h after adding into; After decompression steams partial solvent, add the dilution of 50mL methylene dichloride, pour in the 100mL frozen water; Separate organic phase, wash saturated NaHCO successively with water
3, saturated NaCl washing, the evaporated under reduced pressure solvent gets pale brown sugar colour slurry; The back with 95% ethanol and a small amount of ether wash the white solid powder, alpha-brominated-2,3,4,6-four-O-ethanoyl Glucopyranose, weight 3.54g, productive rate 67%, mp.87-89 ℃ (lit.88-89 ℃)
[43]
With step preparation, alpha-brominated-2,3,4,6-four-O-ethanoyl galactopyranose, mp.74-76 ℃, alpha-brominated-2 ', 3 ', 4 ', 6 ', 2,4,6-seven-O-ethanoyl pyrans lactose, mp.122-124 ℃, alpha-brominated-2,3,4,6-four-O-benzoyl xylopyranose, mp.135-137 ℃, alpha-brominated-2,3,4,6-four-O-benzoyl ribopyranose, mp.121-122 ℃;
III: the 4-hydroxy benzaldehyde 2.44g that gets 20mmol, the sodium hydroxide 0.84g of 21mmol, 2mmol Tetrabutyl amonium bromide 0.64g, water 10ml, trichloromethane 10mL contains in the 100mL there-necked flask, and 50 ℃ are stirred to dissolving fully, and the back slowly drips the chloroform soln 25mL that contains bromo acetyl glucosamine 8.22g of 20mmol, continue reaction 6h, TLC tracks to and reacts completely; Separate organic phase, 1M NaOH washing, washing each 2 times, anhydrous magnesium sulfate drying, evaporated under reduced pressure solvent; obtain 4-formyl radical phenyl-2,3,4 through silica gel column chromatography, 6-four-O-ethanoyl-β-D-glucopyranoside; white solid, heavy 4.55g, productive rate 50%, mp.142-143 ℃.
2. according to the preparation method of claim 1 some glucoside, it is characterized in that: described each component mark and per-cent unless otherwise indicated, all to calculate by weight.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2010101972445A CN101875675A (en) | 2010-06-11 | 2010-06-11 | Preparation method of some glucoside |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2010101972445A CN101875675A (en) | 2010-06-11 | 2010-06-11 | Preparation method of some glucoside |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN101875675A true CN101875675A (en) | 2010-11-03 |
Family
ID=43018367
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2010101972445A Pending CN101875675A (en) | 2010-06-11 | 2010-06-11 | Preparation method of some glucoside |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN101875675A (en) |
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102731582A (en) * | 2012-07-09 | 2012-10-17 | 济南圣泉唐和唐生物科技有限公司 | Preparation method of acetyl halogenated saccharide |
| CN102863479A (en) * | 2011-11-04 | 2013-01-09 | 济南圣泉唐和唐生物科技有限公司 | Method for preparing all-acetyl bromo-L-arabinose |
| CN102942602A (en) * | 2012-12-06 | 2013-02-27 | 济南圣泉唐和唐生物科技有限公司 | Preparation method of o-nitrobenzene galactoside |
| CN103265586A (en) * | 2013-06-06 | 2013-08-28 | 济南卡博唐生物科技有限公司 | Method for preparing dodecyl maltoside from maltose |
| CN103923133A (en) * | 2014-01-17 | 2014-07-16 | 中国科学院昆明植物研究所 | Method for preparing alpha-arbutin |
| CN104478953A (en) * | 2014-11-12 | 2015-04-01 | 川渝中烟工业有限责任公司 | Method for preparing cigarette fragrance releaser with honey sweet note |
| CN106397504A (en) * | 2016-08-31 | 2017-02-15 | 重庆欣欣向荣精细化工有限公司 | Method for producing penta-acetyl glucose |
| CN108823269A (en) * | 2018-05-17 | 2018-11-16 | 金华市艾力生物科技有限公司 | The preparation method of fish collagen oligopeptide |
| CN108997452A (en) * | 2018-07-06 | 2018-12-14 | 陕西中医药大学 | A kind of synthetic method of acetylation Stibene-glucoside |
| CN109776630A (en) * | 2019-02-26 | 2019-05-21 | 佛山科学技术学院 | Lactose base mercaptopropionic acid root or galactosyl mercaptopropionic acid root and its preparation method and application |
| CN111100102A (en) * | 2019-11-22 | 2020-05-05 | 吉尔生化（上海）有限公司 | Preparation method of 3, 4, 6-O-triacetyl-D-glucal |
| CN111434672A (en) * | 2019-01-14 | 2020-07-21 | 天津科技大学 | Preparation method of glycyrrhetinic acid glucoside and application of glycyrrhetinic acid glucoside in sweetener |
-
2010
- 2010-06-11 CN CN2010101972445A patent/CN101875675A/en active Pending
Cited By (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102863479A (en) * | 2011-11-04 | 2013-01-09 | 济南圣泉唐和唐生物科技有限公司 | Method for preparing all-acetyl bromo-L-arabinose |
| CN102863479B (en) * | 2011-11-04 | 2015-06-17 | 济南圣泉唐和唐生物科技有限公司 | Method for preparing all-acetyl bromo-L-arabinose |
| CN102731582A (en) * | 2012-07-09 | 2012-10-17 | 济南圣泉唐和唐生物科技有限公司 | Preparation method of acetyl halogenated saccharide |
| CN102731582B (en) * | 2012-07-09 | 2014-11-19 | 济南圣泉唐和唐生物科技有限公司 | Preparation method of acetyl halogenated saccharide |
| CN102942602B (en) * | 2012-12-06 | 2015-09-23 | 济南圣泉唐和唐生物科技有限公司 | The preparation method of o-nitrophenyl galactoside |
| CN102942602A (en) * | 2012-12-06 | 2013-02-27 | 济南圣泉唐和唐生物科技有限公司 | Preparation method of o-nitrobenzene galactoside |
| CN103265586A (en) * | 2013-06-06 | 2013-08-28 | 济南卡博唐生物科技有限公司 | Method for preparing dodecyl maltoside from maltose |
| CN103265586B (en) * | 2013-06-06 | 2016-02-03 | 济南尚博生物科技有限公司 | A kind of method being prepared Lauryl.beta.-maltoside by maltose |
| CN103923133A (en) * | 2014-01-17 | 2014-07-16 | 中国科学院昆明植物研究所 | Method for preparing alpha-arbutin |
| CN103923133B (en) * | 2014-01-17 | 2016-08-31 | 大兴安岭林格贝寒带生物科技股份有限公司 | A kind of method preparing alpha-arbutin |
| CN104478953A (en) * | 2014-11-12 | 2015-04-01 | 川渝中烟工业有限责任公司 | Method for preparing cigarette fragrance releaser with honey sweet note |
| CN106397504A (en) * | 2016-08-31 | 2017-02-15 | 重庆欣欣向荣精细化工有限公司 | Method for producing penta-acetyl glucose |
| CN108823269A (en) * | 2018-05-17 | 2018-11-16 | 金华市艾力生物科技有限公司 | The preparation method of fish collagen oligopeptide |
| CN108997452A (en) * | 2018-07-06 | 2018-12-14 | 陕西中医药大学 | A kind of synthetic method of acetylation Stibene-glucoside |
| CN111434672A (en) * | 2019-01-14 | 2020-07-21 | 天津科技大学 | Preparation method of glycyrrhetinic acid glucoside and application of glycyrrhetinic acid glucoside in sweetener |
| CN109776630A (en) * | 2019-02-26 | 2019-05-21 | 佛山科学技术学院 | Lactose base mercaptopropionic acid root or galactosyl mercaptopropionic acid root and its preparation method and application |
| CN111100102A (en) * | 2019-11-22 | 2020-05-05 | 吉尔生化（上海）有限公司 | Preparation method of 3, 4, 6-O-triacetyl-D-glucal |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN101875675A (en) | Preparation method of some glucoside | |
| Barbosa et al. | Structural characterization of Botryosphaeran: a (1→ 3; 1→ 6)-β-d-glucan produced by the ascomyceteous fungus, Botryosphaeria sp. | |
| Gamian et al. | Structure of the L2 lipopolysaccharide core oligosaccharides of Neisseria meningitidis. | |
| Fujishima et al. | Isolation and structural analysis in vivo of newly synthesized fructooligosaccharides in onion bulbs tissues (Allium cepa L.) during storage | |
| Mandal et al. | Chemical analysis of new water-soluble (1→ 6)-,(1→ 4)-α, β-glucan and water-insoluble (1→ 3)-,(1→ 4)-β-glucan (Calocyban) from alkaline extract of an edible mushroom, Calocybe indica (Dudh Chattu) | |
| CN103435714B (en) | The preparation of the thick polysaccharide of a kind of fig and purification process and purposes | |
| CN104151373A (en) | Lignan glycoside compounds and preparation method thereof | |
| Wang et al. | Glucosylation of steroidal saponins by cyclodextrin glucanotransferase | |
| Uriel et al. | Unexpected Stereocontrolled Access to 1α, 1′ β-Disaccharides from Methyl 1, 2-Ortho Esters | |
| Aoki et al. | Structural elucidation of a novel transglycosylated compound α-glucosyl rhoifolin and of α-glucosyl rutin by NMR spectroscopy | |
| CN103709209B (en) | The preparation method of isopropyl-β-D-thiogalactoside | |
| CN108892740B (en) | Synthesis method of 3, 6-branched glucan hexaose | |
| CN103539871B (en) | To the method for the uncle position highly selective acylation of complete trimethyl silicon based guard ring dextrin | |
| CN108276461A (en) | A kind of cheap synthetic method of Ethyl vanillin-β-D- glucopyranosides | |
| CN109336856A (en) | A kind of preparation method of the bromo- D- glucal of 6- | |
| Tatsuzawa et al. | Triacylated cyanidin 3-(3X-glucosylsambubioside)-5-glucosides from the flowers of Malcolmia maritima | |
| CN104561220A (en) | Method for preparing tomatidine through cellulose hydrolysis of tomato branches and leaves | |
| CN102746347B (en) | A kind of method of purification of CAPG | |
| CN107216359A (en) | A kind of synthetic method of β ursin | |
| CN107955050A (en) | A kind of auxiliary color extracting method of blackberry anthocyanin extraction assistant agent and blackberry anthocyanin | |
| Levene et al. | PENTAMETHYL GLUCOSE AND ITS DIMETHYL ACETAL. | |
| Miranda et al. | Ferric chloride: a mild and versatile reagent for the formation of 1, 6-anhydro glucopyranoses | |
| Zacharia et al. | Facile synthesis of acacetin-7-O-β-d-galactopyranoside | |
| CN105037455B (en) | The synthetic method of alkyl β D glucopyranosides | |
| Liu et al. | Steroidal glycosides from the fruits of Tribulus terrestris |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C02 | Deemed withdrawal of patent application after publication (patent law 2001) | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20101103 |