CN108276461A - A kind of cheap synthetic method of Ethyl vanillin-β-D- glucopyranosides - Google Patents
A kind of cheap synthetic method of Ethyl vanillin-β-D- glucopyranosides Download PDFInfo
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Abstract
The invention discloses a kind of cheap synthetic methods of Ethyl vanillin β D glucopyranosides; for the tetra-acetylated glucose of α bromos with Ethyl vanillin under 20~80 DEG C, anhydrous, alkaline condition, reaction generates four O acetyl group β D glucopyranosides of Ethyl vanillin；Deacetylation obtains Ethyl vanillin β D glucopyranosides to four O acetyl group β D glucopyranosides of Ethyl vanillin again.The synthetic method of the present invention is not only of low cost, easy to operate, and avoids the use of the mercury salt of expensive silver carbonate or severe toxicity and the pyridine with bad smell, is suitble to industrialized production.
Description
Technical field
The invention belongs to the synthesis technical fields of Ethyl vanillin-β-D- glucopyranosides, and in particular to a kind of ethyl
The cheap synthetic method of vanillic aldehyde-β-D- glucopyranosides.
Background technology
Glucosides is a kind of important latent Studies of The Aromatic Substances, be monosaccharide or oligosaccharide hemiacetal hydroxyl and another molecule in hydroxyl
The dehydrations such as base, amino and the compound generated.After flavor molecule and glucose etc. are combined into glucosides, do not have volatility or volatility
It is very low, therefore stability greatly improves.The fragrance object of many glycoside forms is found in tobacco, fruit, drinks and other products
Matter.For example, Ethyl vanillin-β-D- glucopyranosides have FEMA, No. GRAS, can use safely.
Phenolic glycoside is one kind of glucosides, and since the nucleophilicity of phenol is poor, the glycosylation generation of phenols is relatively difficult.Phenolic glycoside class
The synthesis for closing object, most frequently using Koenigs-Knorr methods.Koenigs-Knorr methods are using bromine or chlorine glycosides as glycosyl
Under the promotion of the catalyst such as silver carbonate or mercuric bromide with receptor glycosylation reaction occurs for donor.The advantages of the method is donor
It is convenient to prepare, and reactivity is good, but the mercury salt of the heavy metal silver salt of needs costliness or severe toxicity makees catalyst, and needs
With being more toxic and the pyridine with bad smell makees alkali.
Invention content
It is an object of the invention in place of overcome the deficiencies in the prior art, provide a kind of Ethyl vanillin-β-D- pyrans
The cheap synthetic method of glucoside, step is short, easy to operate, raw material is easy to get, reaction condition is mild, obtains purpose in high yield
Object is closed, avoids the mercury salt using expensive silver carbonate or severe toxicity, while also avoiding the pyridine with bad smell.
The technical solution adopted by the present invention to solve the technical problems is：
A kind of synthetic method of Ethyl vanillin-β-D- glucopyranosides, including：
1) Ethyl vanillin shown in alpha-brominated tetra-acetylated glucose shown in formula II and formula III is in 20~80 DEG C, nothing
Under water, alkaline condition, four-O- acetyl group-β-D- glucopyranosides of Ethyl vanillin shown in production IV are reacted；The step
1) it can be indicated with following reaction equation：
2) four-O- acetyl group-β-D- glucopyranoside deacetylations of Ethyl vanillin shown in formula IV obtain shown in formula I
Ethyl vanillin-β-D- glucopyranosides；The step 2) can be indicated with following reaction equation：
In the step 1), the molar ratio of the alpha-brominated tetra-acetylated glucose and Ethyl vanillin is 1:1~2.
In the step 1), the reaction of IV compound of production carries out under alkaline condition, and alkaline condition is by appropriate
Alkali carries supply, the alkali is sodium carbonate, sodium bicarbonate, potassium carbonate, at least one of cesium carbonate.
In the step 1), the reaction of IV compound of production carries out in the first solvent appropriate, and described first
Solvent is at least one of triethylamine, diisopropyl ethyl amine, Tri-n-Propylamine, N- crassitudes, N-methylmorpholine.
In the step 1), the anhydrous condition of the reaction of IV compound of production by adding 4A molecules in the reaction system
Sieve is realized.
In the step 1), the reaction temperature of IV compound of production is 25~75 DEG C.
In the step 1), the reaction time of IV compound of production is 1~48h.
In the step 1), the dosage of the alkali is 1.0~10.0 equivalents of alpha-brominated tetra-acetylated glucose.
In the step 2), the deacetylation for generating type I compound carries out under alkaline condition, alkaline condition
It is supplied by alkali carries appropriate, the alkali is sodium carbonate, potassium carbonate, sodium methoxide, sodium ethoxide, sodium tert-butoxide, sodium hydroxide, potassium hydroxide
At least one of.
In the step 2), the deacetylation for generating type I compound carries out in the second solvent appropriate, institute
It is at least one of methanol, ethyl alcohol, the tert-butyl alcohol, tetrahydrofuran, acetone, N,N-dimethylformamide to state the second solvent.
Specifically, operation process is as follows：
1) be added in reaction bulb alpha-brominated tetra-acetylated glucose, Ethyl vanillin shown in formula III shown in formula II,
Alkali, the first solvent and 4A molecular sieves react 1~48h at 25~75 DEG C.After having reacted, organic solvent diluting system, mistake is added
Insoluble matter is filtered out, water extracting and demixing is then added.Organic phase is dried and concentrated after alkali liquid washing, the residue that will be obtained
By column chromatography for separation to get four-O- acetyl group-β-D- glucopyranosides of Ethyl vanillin shown in formula IV；
2) in reaction bulb be added formula IV shown in four-O- acetyl group-β-D- glucopyranosides of Ethyl vanillin, alkali and
Second solvent, at 20~60 DEG C react 1~for 24 hours.After having reacted, system is neutralized to pH=6.5, solvent is removed under reduced pressure, will
The residue arrived is by column chromatography for separation up to product.
Compared with the background art, it has the following advantages that the technical program：
The advantage of the invention is that：Under the alkaline condition that the solvent of alkali, alkalinity is constituted, by brief route, simply
Operation, be prepared for Ethyl vanillin-β-D- glucopyranosides in high yield.The route is not only of low cost, easy to operate,
The mercury salt using expensive silver carbonate or severe toxicity is avoided, while also avoiding the pyridine with bad smell, is suitble to industrialization
Production.
Specific implementation mode
Present disclosure is illustrated below by embodiment：
Embodiment 1
1) synthesis of four-O- acetyl group-β-D- glucopyranosides of Ethyl vanillin：
Be added in reaction bulb alpha-brominated tetra-acetylated glucose (8.22g, 20.0mmol), potassium carbonate (4.14g,
30.0mmol), triethylamine (80mL), Ethyl vanillin (4.98g, 30.0mmol).4A molecular sieves (2.0g), heating is then added
It is stirred to react 20h to 50 DEG C.It is tracked and is reacted with TLC.After completion of the reaction, 100mL ethyl acetate is added, is then filtered to remove insoluble
Object.100mL water is added, fully liquid separation obtains organic phase after oscillation.Organic phase uses unsaturated carbonate potassium solution and saturated common salt successively again
Water washing is concentrated to give grease after after anhydrous magnesium sulfate is dried.Grease is subjected to column chromatography for separation (petroleum ether：Acetic acid
Ethyl ester=1:1) the half liquid substances admittedly of 8.14g half, are obtained, yield 82% is four-O- acetyl group-β-D- pyrans of Ethyl vanillin
Glucoside.
ESI-MS(m/z):497[M+H]+；1H NMR(400MHz,CDCl3)δ:1.43-1.46 (t, J=6.8Hz, 3H),
2.02-2.09 (m, 12H), 3.85-3.89 (m, 1H), 4.08-4.13 (q, J=7.2Hz, 2H), 4.17-4.21 (dd, J=12,
2Hz, 1H), 4.26-4.30 (dd, J=12,4.8Hz, 1H), 5.14-5.21 (m, 2H), 5.29-5.37 (m, 2H), 7.19-
7.21 (d, J=8.4Hz, 1H), 7.39-7.42 (m, 2H), 9.88 (s, 1H).
2) synthesis of Ethyl vanillin-β-D- glucopyranosides：
In reaction bulb, sodium methoxide (0.54g, 10.0mmol) and methanol (10mL) are sequentially added, it is fragrant that ethyl is then added
Lan Susi-O- acetyl group-β-D- glucopyranosides (4.96g, 10.0mmol) react 1h at 30 DEG C.After reaction, it is added
In hydrogen chloride methanol solution and system is to pH=6.5.Solvent, column chromatography for separation (dichloromethane is removed under reduced pressure：Methanol=10:1),
3.02g white powders, yield 92% are obtained, 189~190 DEG C of mp is Ethyl vanillin-β-D- glucopyranosides.
ESI-MS(m/z):329[M+H]+；1H NMR(400MHz,CDCl3)δ:1.42-1.45 (t, J=7.0Hz, 3H),
3.40-3.54(m,4H),3.68-3.71(m,1H),3.87-3.89(m,1H),4.15-4.18(m,2H),4.89(s,4H),
5.07-5.09 (d, J=7.0Hz, 1H), 7.30-7.32 (d, J=8.0Hz, 1H), 7.48 (s, 1H), 7.49-7.52 (d, J=
8.4Hz,1H),9.82(s,1H)。
Embodiment 2
1) synthesis of four-O- acetyl group-β-D- glucopyranosides of Ethyl vanillin：
Be added in reaction bulb alpha-brominated tetra-acetylated glucose (8.22g, 20.0mmol), sodium carbonate (3.18g,
30.0mmol), diisopropyl ethyl amine (80mL), Ethyl vanillin (4.98g, 30.0mmol).4A molecular sieves are then added
(2.0g) is heated to 40 DEG C and is stirred to react 30h.It is tracked and is reacted with TLC.After completion of the reaction, 100mL ethyl acetate is added, then
It is filtered to remove insoluble matter.100mL water is added, fully liquid separation obtains organic phase after oscillation.Organic phase uses saturated sodium carbonate molten successively again
Liquid and saturated common salt water washing are concentrated to give grease after after anhydrous magnesium sulfate is dried.Grease is subjected to column chromatography for separation
(petroleum ether：Ethyl acetate=1:1) the half liquid substances admittedly of 7.73g half, are obtained, yield 78% is four-O- acetyl of Ethyl vanillin
Base-β-D- glucopyranosides.
2) synthesis of Ethyl vanillin-β-D- glucopyranosides：
In reaction bulb, sodium tert-butoxide (0.96g, 10.0mmol) and the tert-butyl alcohol (10mL) are sequentially added, second is then added
Four-O- acetyl group-β-D- glucopyranosides (4.96g, 10.0mmol) of base vanillic aldehyde react 1h at 30 DEG C.After reaction,
It is added in hydrogen chloride methanol solution and system to pH=6.5.Solvent, column chromatography for separation (dichloromethane is removed under reduced pressure：Methanol=
10:1) 2.89g white powders, are obtained, yield 88% is Ethyl vanillin-β-D- glucopyranosides.
Embodiment 3
1) synthesis of four-O- acetyl group-β-D- glucopyranosides of Ethyl vanillin：
Be added in reaction bulb alpha-brominated tetra-acetylated glucose (8.22g, 20.0mmol), cesium carbonate (9.77g,
30.0mmol), triethylamine (80mL), Ethyl vanillin (4.98g, 30.0mmol).4A molecular sieves (2.0g), heating is then added
It is stirred to react 10h to 60 DEG C.It is tracked and is reacted with TLC.After completion of the reaction, 100mL ethyl acetate is added, is then filtered to remove insoluble
Object.100mL water is added, fully liquid separation obtains organic phase after oscillation.Organic phase uses saturated sodium carbonate solution and saturated common salt successively again
Water washing is concentrated to give grease after after anhydrous magnesium sulfate is dried.Grease is subjected to column chromatography for separation (petroleum ether：Acetic acid
Ethyl ester=1:1) the half liquid substances admittedly of 7.14g half, are obtained, yield 72% is four-O- acetyl group-β-D- pyrans of Ethyl vanillin
Glucoside.
2) synthesis of Ethyl vanillin-β-D- glucopyranosides：
In reaction bulb, sodium ethoxide (0.68g, 10.0mmol) and ethyl alcohol (10mL) are sequentially added, it is fragrant that ethyl is then added
Lan Susi-O- acetyl group-β-D- glucopyranosides (4.96g, 10.0mmol) react 1h at 30 DEG C.After reaction, it is added
In ethanol solution of hydrogen chloride and system is to pH=6.5.Solvent, column chromatography for separation (dichloromethane is removed under reduced pressure：Methanol=10:1),
2.95g white powders are obtained, yield 90% is Ethyl vanillin-β-D- glucopyranosides.
Embodiment 4
1) synthesis of four-O- acetyl group-β-D- glucopyranosides of Ethyl vanillin：
Be added in reaction bulb alpha-brominated tetra-acetylated glucose (8.22g, 20.0mmol), potassium carbonate (4.14g,
30.0mmol), N- crassitudes (80mL), Ethyl vanillin (4.98g, 30.0mmol).4A molecular sieves are then added
(2.0g) is heated to 50 DEG C and is stirred to react 20h.It is tracked and is reacted with TLC.After completion of the reaction, 100mL ethyl acetate is added, then
It is filtered to remove insoluble matter.100mL water is added, fully liquid separation obtains organic phase after oscillation.Organic phase uses saturated potassium carbonate molten successively again
Liquid and saturated common salt water washing are concentrated to give grease after after anhydrous magnesium sulfate is dried.Grease is subjected to column chromatography for separation
(petroleum ether：Ethyl acetate=1:1) the half liquid substances admittedly of 8.43g half, are obtained, yield 85% is four-O- acetyl of Ethyl vanillin
Base-β-D- glucopyranosides.
2) synthesis of Ethyl vanillin-β-D- glucopyranosides：
In reaction bulb, sodium methoxide (0.54g, 10.0mmol) and methanol (10mL) are sequentially added, it is fragrant that ethyl is then added
Lan Susi-O- acetyl group-β-D- glucopyranosides (4.96g, 10.0mmol) react 1h at 30 DEG C.After reaction, it is added
In hydrogen chloride methanol solution and system is to pH=6.5.Solvent, column chromatography for separation (dichloromethane is removed under reduced pressure：Methanol=10:1),
3.02g white powders, yield 92% are obtained, 189~190 DEG C of mp is Ethyl vanillin-β-D- glucopyranosides.
The above, only present pre-ferred embodiments, therefore cannot limit the scope of implementation of the present invention according to this, i.e., according to
Equivalent changes and modifications made by the scope of the claims of the present invention and description all should still belong in the range of the present invention covers.
Claims (10)
1. a kind of synthetic method of Ethyl vanillin-β-D- glucopyranosides, it is characterised in that：Including：
1) Ethyl vanillin shown in alpha-brominated tetra-acetylated glucose shown in formula II and formula III is in 20~80 DEG C, anhydrous, alkali
Property under the conditions of, react production IV shown in four-O- acetyl group-β-D- glucopyranosides of Ethyl vanillin；
2) four-O- acetyl group-β-D- glucopyranoside deacetylations of Ethyl vanillin shown in formula IV obtain second shown in formula I
Base vanillic aldehyde-β-D- glucopyranosides；
2. the synthetic method of Ethyl vanillin-β-D- glucopyranosides according to claim 1, it is characterised in that：Institute
It states in step 1), the molar ratio of the alpha-brominated tetra-acetylated glucose and Ethyl vanillin is 1:1~2.
3. the synthetic method of Ethyl vanillin-β-D- glucopyranosides according to claim 1, it is characterised in that：Institute
It states in step 1), the alkaline condition of the reaction of IV compound of production is supplied by alkali carries, and the alkali is sodium carbonate, sodium bicarbonate, carbon
At least one of sour potassium, cesium carbonate.
4. the synthetic method of Ethyl vanillin-β-D- glucopyranosides according to claim 1, it is characterised in that：Institute
It states in step 1), the reaction of IV compound of production carries out in the first solvent, and first solvent is triethylamine, diisopropyl
At least one of ethylamine, Tri-n-Propylamine, N- crassitudes, N-methylmorpholine.
5. the synthetic method of Ethyl vanillin-β-D- glucopyranosides according to claim 1, it is characterised in that：Institute
It states in step 1), the anhydrous condition of the reaction of IV compound of production is realized by adding 4A molecular sieves in the reaction system.
6. the synthetic method of Ethyl vanillin-β-D- glucopyranosides according to claim 1, it is characterised in that：Institute
It states in step 1), the reaction temperature of IV compound of production is 25~75 DEG C.
7. the synthetic method of Ethyl vanillin-β-D- glucopyranosides according to claim 1, it is characterised in that：Institute
It states in step 1), the reaction time of IV compound of production is 1~48h.
8. the synthetic method of Ethyl vanillin-β-D- glucopyranosides according to claim 3, it is characterised in that：Institute
It states in step 1), the dosage of the alkali is 1.0~10.0 equivalents of alpha-brominated tetra-acetylated glucose.
9. the synthetic method of Ethyl vanillin-β-D- glucopyranosides according to claim 1, it is characterised in that：Institute
It states in step 2), the deacetylation for generating type I compound carries out under alkaline condition, and the alkaline condition is supplied by alkali carries,
The alkali is at least one of sodium carbonate, potassium carbonate, sodium methoxide, sodium ethoxide, sodium tert-butoxide, sodium hydroxide, potassium hydroxide.
10. the synthetic method of Ethyl vanillin-β-D- glucopyranosides according to claim 1, it is characterised in that：Institute
It states in step 2), the deacetylation for generating type I compound carries out in the second solvent, and second solvent is methanol, second
At least one of alcohol, the tert-butyl alcohol, tetrahydrofuran, acetone, N,N-dimethylformamide.
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Cited By (2)
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| CN109762794A (en) * | 2018-12-29 | 2019-05-17 | 浙江工业大学 | A kind of application of glucosyltransferase in production Ethyl vanillin-alpha-D-glucose glycosides |
| CN111647461A (en) * | 2020-05-14 | 2020-09-11 | 湖北中烟工业有限责任公司 | Spice for cigarette not burning by heating, preparation method and cigarette not burning by heating |
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| CN109762794A (en) * | 2018-12-29 | 2019-05-17 | 浙江工业大学 | A kind of application of glucosyltransferase in production Ethyl vanillin-alpha-D-glucose glycosides |
| CN111647461A (en) * | 2020-05-14 | 2020-09-11 | 湖北中烟工业有限责任公司 | Spice for cigarette not burning by heating, preparation method and cigarette not burning by heating |
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