CN104262422A - A chemical synthesis method of 4-(3,4-dihydroxybenzoyloxymethyl)-phenyl-O-beta-D-glucopyranoside - Google Patents
A chemical synthesis method of 4-(3,4-dihydroxybenzoyloxymethyl)-phenyl-O-beta-D-glucopyranoside Download PDFInfo
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- glucopyranoside
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- dihydroxybenzoyl
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Abstract
A chemical synthesis method of 4-(3,4-dihydroxybenzoyloxymethyl)-phenyl-O-beta-D-glucopyranoside is disclosed. The method includes following steps of: reacting 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl bromide and p-hydroxybenzyl alcohol in a dry solvent under the action of an accelerant to obtain 4-hydroxymethylphenyl-O-beta-D-2,3,4,6-tetra-O-acetyl glucopyranoside; reacting the 4-hydroxymethylphenyl-O-beta-D-2,3,4,6-tetra-O-acetyl glucopyranoside and 3,4-diacetoxybenzoyl chloride to obtain 4-(3,4-diacetoxybenzoyloxymethyl)-phenyl-O-beta-D-2,3,4,6-tetra-O-acetyl glucopyranoside; and removing protective groups of the 4-(3,4-diacetoxybenzoyloxymethyl)-phenyl-O-beta-D-2,3,4,6-tetra-O-acetyl glucopyranoside to obtain the target product that is the 4-(3,4-dihydroxybenzoyloxymethyl)-phenyl-O-beta-D-glucopyranoside. The method has characteristics of cheap and easily available raw materials, short reaction steps, convenient separation, low preparation cost, little three-waste discharge, and suitability for industrial production.
Description
Technical field
The invention belongs to field of fine chemical, be specifically related to a kind of chemosynthesis 4-(3,4-dihydroxybenzoyl oxygen methyl)-phenyl-
othe method of-β-D-glucopyranoside.
Background technology
4-(3,4-dihydroxybenzoyl oxygen methyl)-phenyl-
o-β-D-glucopyranoside is a kind of Polyphenols glucoside of separation and Extraction from herbal medicine wild marjoram; there is anti-oxidant and scavenging free radicals function; liver cell and skin cells can be protected from oxidative damage; thus makeup and foodstuff additive [Chia-Hua Liang, Leong-Peng Chan, Hisou-Yu Ding can be used as; et al.; J. Agri. Food and Chem., 2012,7690-7696].But, 4-(3,4-dihydroxybenzoyl oxygen methyl)-phenyl-
othe content of-β-D-glucopyranoside in wild marjoram very low (only 0.083%) [Nobuji Nakatani, Hiroe Kikuzaki, Agri. Biol. Chem., 1987,51 (10), 2727-2732], from wild marjoram, extract 4-(3,4-dihydroxybenzoyl oxygen methyl)-phenyl-
o-β-D-glucopyranoside is very uneconomical, and destroys ecological resources, therefore studies 4-(3,4-dihydroxybenzoyl oxygen methyl)-phenyl-
othe synthesis of-β-D-glucopyranoside is significant.
Summary of the invention
In view of from wild marjoram separation and Extraction 4-(3,4-dihydroxybenzoyl oxygen methyl)-phenyl-
oit is high to there is cost in-β-D-glucopyranoside, destroys the drawback such as ecological resources, and the present inventor develops one on the basis of large quantity research in early stage can chemosynthesis 4-(3,4-dihydroxybenzoyl oxygen methyl in a large number)-phenyl-
othe method of-β-D-glucopyranoside.
The object of this invention is to provide a kind of easy to operate, cost is low, can mass-producing synthesis 4-(3,4-dihydroxybenzoyl oxygen methyl)-phenyl-
othe method of-β-D-glucopyranoside.
Chemosynthesis 4-(3,4-dihydroxybenzoyl oxygen methyl of the present invention)-phenyl-
othe method of-β-D-glucopyranoside, its step is as follows:
1) by 2,3,4,6-tetra--
o-ethanoyl-α-D-bromo Glucopyranose with to hydroxy-benzyl alcohol in the dipolar aprotic solvent of drying, under the catalysis of Anhydrous potassium carbonate and cesium chloride promotor obtained 4-hyd roxymethyl phenyl-
o-β-D-2,3,4,6-tetra--
o-ethanoyl glucopyranoside;
2) 4-hyd roxymethyl phenyl step 1) obtained-
o-β-D-2,3,4,6-tetra--
o-ethanoyl glucopyranoside and 3,4-diacetoxy Benzoyl chloride are obtained by reacting 4-(3 in dry chlorinated hydrocarbon organic solvent and acid binding agent, 4-diacetoxy benzoyloxymethy)-phenyl
o-β-D-2,3,4,6-tetra--
o-ethanoyl glucopyranoside;
3) by step 2) 4-(3 that obtains, 4-diacetoxy benzoyloxymethy)-phenyl
o-β-D-2,3,4,6-tetra--
o-ethanoyl glucopyranoside in absolute alcohol kind solvent under the catalysis of tin type oxide the Acetyl Protecting Groups sloughed on sugared ring and phenyl ring obtain target product 4-(3,4-dihydroxybenzoyl oxygen methyl)-phenyl-
o-β-D-glucopyranoside.
Chemosynthesis 4-(3,4-dihydroxybenzoyl oxygen methyl of the present invention)-phenyl-
othe reaction formula of-β-D-glucopyranoside is as follows, wherein structural formula
1for 4-(3,4-dihydroxybenzoyl oxygen methyl)-phenyl-
o-β-D-glucopyranoside, structural formula
2be 2,3,4,6-tetra--
o-ethanoyl-α-D-bromo Glucopyranose, structural formula
3for p-Hydroxybenzylalcohol, structural formula
4for 4-hyd roxymethyl phenyl-
o-β-D-2,3,4,6-tetra--
o-ethanoyl glucopyranoside, structural formula
5be 3,4-diacetoxy Benzoyl chloride, structural formula
6for 4-(3,4-diacetoxy benzoyloxymethy)-phenyl
o-β-D-2,3,4,6-tetra--
o-ethanoyl glucopyranoside.
Benefit of the present invention is: reactions steps is few, and reaction raw materials is cheap and easy to get, and each step reaction product is without the need to column chromatography for separation, and cost is low, and three waste discharge is few, is suitable for suitability for industrialized production.
Embodiment
Embodiment 1
By 2,3,4,6-tetra--
o-ethanoyl-α-D-bromo Glucopyranose (50mmol; 20.5g) be dissolved in 50 milliliters of dry DMF; add p-Hydroxybenzylalcohol (55mmol; 6.85g) and Anhydrous potassium carbonate (60mmol; 8.3g); add catalytic amount (2.5mmol; 0,42g) cesium chloride, room temperature reaction 2 hours; by in reaction mixture impouring frozen water; separate out white solid, collecting by filtration white solid, gained white solid dehydrated alcohol recrystallization obtains white crystal 16.2g; yield 71%, fusing point 108.9-109.7 DEG C.
1HNMR(400MHz, CDCl
3) d 2.04, 2.05, 2.06, 2.08 (4 s, each 3H, 4OCOC
H 3), 3.84-3.88（m, 1H, H-5）, 4.18（dd,
J = 12.4Hz, 4.2Hz, 1H, H-6a）, 4.29（dd,
J = 12.4Hz, 5.2Hz, 1H, H-6b）, 4.64 ( s, 2H, ArC
H 2OH), 5.07（d,
J = 7.2 Hz, 1H, H-1）, 5.16（t,
J = 9.6Hz, 1H, H-4）, 5.24-5.32（m, 2H, H-2, H-5）, 6.98（d,
J =8.4 Hz, 2H, Ar-
H ）, 7.27-7.31（m, 2H, Ar-
H）。
By above-mentioned obtained 4-hyd roxymethyl phenyl-
o-β-D-2,3,4,6-tetra--
o-ethanoyl glucopyranoside (20mmol; 9.08g) dissolve in 50ml dry methylene chloride; add acid binding agent triethylamine (22mmol; 2.22g); (21mmol is dripped under ice bath; 5.38g) 3,4-diacetoxy Benzoyl chlorides are at the solution of 10ml methylene dichloride, finish; remove ice bath; room temperature reaction 2 hours, reaction mixture uses water, saturated common salt water washing successively, separates dichloromethane layer; concentrating under reduced pressure obtains light yellow solid; white crystal 12.4g is obtained, yield 92.1%, fusing point 57-58 DEG C with dehydrated alcohol recrystallization.
1HNMR(400MHz, CDCl
3) d 2.03, 2.04, 2.7, 2.08 (4 s, each 3H, 4OCOC
H 3), 2.32(s, 6H, ArOAc), 3.85(ddd,
J = 10.0, 5.4, 2.0 Hz, 1H ), 4.18(dd,
J = 12.4, 2.4 Hz , 1H ), 4.27(dd,
J = 12.4, 5.4 Hz, 1H ), 5.08(d,
J = 7.3Hz, 1H ), 5.17(t,
J = 9.5Hz, 1H ), 5.24-5.33(m, 2H), 5.31(s, 2H), 7.02(d,
J = 8.6Hz, 2H ), 7.29(d,
J = 8.5Hz, 1H ), 7.36(d,
J = 8.6Hz, 2H ), 7.85(d,
J = 1.9Hz,1H ),7.98
(dd,
J = 8.5, 1.9 Hz, 1H )。
By above-mentioned obtained 4-(3,4-diacetoxy benzoyloxymethy)-phenyl
o-β-D-2,3,4,6-tetra--
o-ethanoyl glucopyranoside
6(15mmol, 10.1g) dissolve in 50ml anhydrous methanol, add catalytic amount Dibutyltin oxide (0.5mmol, 0.125g) heating reflux reaction 3 hours, concentrating under reduced pressure, resistates dehydrated alcohol-chloroform mixed solvent recrystallization (chloroform: dehydrated alcohol 8:1) obtains white crystal 5.76g, yield 92%, fusing point 203-204 DEG C.
1HNMR(400MHz, CD
3OD) d3.32-3.48 (m, 4H ), 3.68(dd,
J = 12.1, 5.4 Hz , 1H ), 3.89(dd,
J = 12.1, 2.1 Hz, 1H ), 4.91 (m, 1H), 6.79(d,
J = 8.1Hz, 1H ), 7.12(d,
J = 8.8Hz, 2H ), 7.38(d,
J = 8.8Hz, 2H ), 7.42 (m, 2H )。
Embodiment 2
By 2,3,4,6-tetra--
o-ethanoyl-α-D-bromo Glucopyranose (0.1mol; 41g) be dissolved in 100 milliliters of dry DMF; add p-Hydroxybenzylalcohol (0.12mol; 7.47g) and Anhydrous potassium carbonate (0.24mol; 16.6g); add catalytic amount (5mmol; cesium chloride 0.84g); 40 DEG C are reacted 2 hours, by reaction mixture impouring frozen water, separate out white solid; collecting by filtration white solid; gained white solid dehydrated alcohol recrystallization obtains white crystal 33.3g, yield 73%, fusing point 108.1-109.4 DEG C.
By above-mentioned obtained 4-hyd roxymethyl phenyl-
o-β-D-2,3,4,6-tetra--
o-ethanoyl glucopyranoside (0.04mol; 18.16g) dissolve in 100ml dry methylene chloride; add acid binding agent triethylamine (0.45mol; 4.45g); (0.42mol is dripped under ice bath; 10.76g) 3,4-diacetoxy Benzoyl chlorides are at the solution of 15ml methylene dichloride, finish; remove ice bath; room temperature reaction 2 hours, reaction mixture uses water, saturated common salt water washing successively, separates dichloromethane layer; concentrating under reduced pressure obtains light yellow solid; white crystal 24.8g is obtained, yield 92.4%, fusing point 57-58 DEG C with dehydrated alcohol recrystallization.
By above-mentioned obtained 4-(3,4-diacetoxy benzoyloxymethy)-phenyl
o-β-D-2,3,4,6-tetra--
o-ethanoyl glucopyranoside
6(0.3mol, 20.2g) dissolve in 100ml anhydrous methanol, add catalytic amount Dibutyltin oxide (1mmol, 0. 25g) heating reflux reaction 3 hours, concentrating under reduced pressure, resistates dehydrated alcohol-chloroform mixed solvent recrystallization (chloroform: dehydrated alcohol 8:1) obtains white crystal 11.56g, yield 92.3%, fusing point 203-204 DEG C.
Claims (5)
1. a chemosynthesis 4-(3,4-dihydroxybenzoyl oxygen methyl)-phenyl-
othe method of-β-D-glucopyranoside, its step is as follows:
By 2,3,4,6-tetra--
o-ethanoyl-α-D-bromo Glucopyranose with to hydroxy-benzyl alcohol in the dipolar aprotic solvent of drying, under the catalysis of Anhydrous potassium carbonate and cesium chloride promotor obtained 4-hyd roxymethyl phenyl-
o-β-D-2,3,4,6-tetra--
o-ethanoyl glucopyranoside;
The 4-hyd roxymethyl phenyl that step 1) is obtained-
o-β-D-2,3,4,6-tetra--
o-ethanoyl glucopyranoside and 3,4-diacetoxy Benzoyl chloride are obtained by reacting 4-(3 in dry chlorinated hydrocarbon organic solvent and acid binding agent, 4-diacetoxy benzoyloxymethy)-phenyl
o-β-D-2,3,4,6-tetra--
o-ethanoyl glucopyranoside;
By step 2) 4-(3 that obtains, 4-diacetoxy benzoyloxymethy)-phenyl
o-β-D-2,3,4,6-tetra--
o-ethanoyl glucopyranoside in absolute alcohol kind solvent under the catalysis of tin type oxide the Acetyl Protecting Groups sloughed on sugared ring and phenyl ring obtain target product 4-(3,4-dihydroxybenzoyl oxygen methyl)-phenyl-
o-β-D-glucopyranoside.
2. according to claim
1described chemical 4-(3,4-dihydroxybenzoyl oxygen methyl)-phenyl-
othe method of-β-D-glucopyranoside, is characterized in that used promotor is cesium chloride.
3. according to claim
1described chemical 4-(3,4-dihydroxybenzoyl oxygen methyl)-phenyl-
othe method of-β-D-glucopyranoside, the dipolar aprotic solvent that it is characterized in that using in glycosylation reaction is acetone, DMF and dimethyl sulfoxide (DMSO).
4. according to claim
1described chemical 4-(3,4-dihydroxybenzoyl oxygen methyl)-phenyl-
othe method of-β-D-glucopyranoside, it is characterized in that the chlorinated hydrocarbon solvent used in esterification is methylene dichloride, Benzene Chloride etc., the acid binding agent used is triethylamine, salt of wormwood etc.
5. according to claim
1described chemical 4-(3,4-dihydroxybenzoyl oxygen methyl)-phenyl-
othe method of-β-D-glucopyranoside, is characterized in that the alcoholic solvent used in deprotection reaction is anhydrous methanol or ethanol, and the tin type oxide catalyzer used is Dibutyltin oxide.
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| CN201410415034.7A CN104262422B (en) | 2014-08-22 | 2014-08-22 | A kind of chemosynthesis 4-(3,4-dihydroxybenzoyl oxygen methyl) method of-phenyl-O-β-D-pyranglucoside |
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| CN201410415034.7A CN104262422B (en) | 2014-08-22 | 2014-08-22 | A kind of chemosynthesis 4-(3,4-dihydroxybenzoyl oxygen methyl) method of-phenyl-O-β-D-pyranglucoside |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN107325136A (en) * | 2017-08-10 | 2017-11-07 | 昆药集团股份有限公司 | A kind of Acegastrodine compound and preparation method thereof, pharmaceutical composition, preparation and application |
| CN107383125A (en) * | 2017-08-15 | 2017-11-24 | 昆药集团股份有限公司 | A kind of Acegastrodine compound and preparation method thereof, preparation and application |
| CN108047285A (en) * | 2017-12-18 | 2018-05-18 | 厦门医学院 | A kind of cheap synthetic method of the glucose phenol glycosides compound of ortho position ester group substitution |
| CN111018928A (en) * | 2019-12-06 | 2020-04-17 | 北京悦康科创医药科技股份有限公司 | Synthetic method and application of gastrodin hemihydrate |
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| CN103275146A (en) * | 2013-06-13 | 2013-09-04 | 青岛农业大学 | Gastrodin chemical synthesis method suitable for industrialization |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107325136A (en) * | 2017-08-10 | 2017-11-07 | 昆药集团股份有限公司 | A kind of Acegastrodine compound and preparation method thereof, pharmaceutical composition, preparation and application |
| CN107383125A (en) * | 2017-08-15 | 2017-11-24 | 昆药集团股份有限公司 | A kind of Acegastrodine compound and preparation method thereof, preparation and application |
| CN108047285A (en) * | 2017-12-18 | 2018-05-18 | 厦门医学院 | A kind of cheap synthetic method of the glucose phenol glycosides compound of ortho position ester group substitution |
| CN108047285B (en) * | 2017-12-18 | 2020-07-03 | 厦门医学院 | Cheap synthesis method of ortho-ester-substituted glucose phenolic glycoside compound |
| CN111018928A (en) * | 2019-12-06 | 2020-04-17 | 北京悦康科创医药科技股份有限公司 | Synthetic method and application of gastrodin hemihydrate |
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