CN117924376A - Preparation method and application of 3, 6-dehydrated-D-glucopyranose - Google Patents
Preparation method and application of 3, 6-dehydrated-D-glucopyranose Download PDFInfo
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- CN117924376A CN117924376A CN202410031348.0A CN202410031348A CN117924376A CN 117924376 A CN117924376 A CN 117924376A CN 202410031348 A CN202410031348 A CN 202410031348A CN 117924376 A CN117924376 A CN 117924376A
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- 238000002360 preparation method Methods 0.000 title claims abstract description 25
- 238000006243 chemical reaction Methods 0.000 claims abstract description 35
- 235000019504 cigarettes Nutrition 0.000 claims abstract description 18
- 239000002994 raw material Substances 0.000 claims abstract description 10
- 235000009508 confectionery Nutrition 0.000 claims abstract description 9
- HOVAGTYPODGVJG-ZFYZTMLRSA-N methyl alpha-D-glucopyranoside Chemical compound CO[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O HOVAGTYPODGVJG-ZFYZTMLRSA-N 0.000 claims abstract 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 36
- 150000001875 compounds Chemical class 0.000 claims description 34
- 239000002904 solvent Substances 0.000 claims description 22
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
- 239000003054 catalyst Substances 0.000 claims description 12
- 239000000047 product Substances 0.000 claims description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 9
- DCQFFOLNJVGHLW-RSVSWTKNSA-N (1r,4r,5s,8r)-2,6-dioxabicyclo[3.2.1]octane-3,4,8-triol Chemical compound O[C@H]1[C@]2([H])OC[C@@]1([H])OC(O)[C@@H]2O DCQFFOLNJVGHLW-RSVSWTKNSA-N 0.000 claims description 8
- 241000208125 Nicotiana Species 0.000 claims description 8
- 235000002637 Nicotiana tabacum Nutrition 0.000 claims description 8
- 239000012074 organic phase Substances 0.000 claims description 7
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 239000007868 Raney catalyst Substances 0.000 claims description 5
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 5
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 5
- 239000012043 crude product Substances 0.000 claims description 5
- 239000000706 filtrate Substances 0.000 claims description 5
- HOVAGTYPODGVJG-UHFFFAOYSA-N methyl beta-galactoside Natural products COC1OC(CO)C(O)C(O)C1O HOVAGTYPODGVJG-UHFFFAOYSA-N 0.000 claims description 5
- 238000010898 silica gel chromatography Methods 0.000 claims description 5
- 239000011734 sodium Substances 0.000 claims description 5
- QXJDESBAUIILLG-UHFFFAOYSA-N 1,2,3,3,4,4,4-heptafluoro-1-iodobut-1-ene Chemical compound FC(I)=C(F)C(F)(F)C(F)(F)F QXJDESBAUIILLG-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 238000001704 evaporation Methods 0.000 claims description 4
- 239000000796 flavoring agent Substances 0.000 claims description 4
- 235000019634 flavors Nutrition 0.000 claims description 4
- OSHOQERNFGVVRH-UHFFFAOYSA-K iron(3+);trifluoromethanesulfonate Chemical compound [Fe+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F OSHOQERNFGVVRH-UHFFFAOYSA-K 0.000 claims description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 4
- GRGCWBWNLSTIEN-UHFFFAOYSA-N trifluoromethanesulfonyl chloride Chemical compound FC(F)(F)S(Cl)(=O)=O GRGCWBWNLSTIEN-UHFFFAOYSA-N 0.000 claims description 4
- 239000003153 chemical reaction reagent Substances 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 3
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 3
- JXRGUPLJCCDGKG-UHFFFAOYSA-N 4-nitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC=C(S(Cl)(=O)=O)C=C1 JXRGUPLJCCDGKG-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000012359 Methanesulfonyl chloride Substances 0.000 claims description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
- GPWHDDKQSYOYBF-UHFFFAOYSA-N ac1l2u0q Chemical compound Br[Br-]Br GPWHDDKQSYOYBF-UHFFFAOYSA-N 0.000 claims description 2
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 claims description 2
- 238000001914 filtration Methods 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 claims description 2
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 claims description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- 230000006103 sulfonylation Effects 0.000 claims description 2
- 238000005694 sulfonylation reaction Methods 0.000 claims description 2
- 235000019605 sweet taste sensations Nutrition 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 3
- 238000003786 synthesis reaction Methods 0.000 abstract description 4
- 206010013911 Dysgeusia Diseases 0.000 abstract description 3
- 239000003205 fragrance Substances 0.000 abstract description 3
- 239000000779 smoke Substances 0.000 abstract description 3
- 210000000214 mouth Anatomy 0.000 abstract description 2
- 230000035699 permeability Effects 0.000 abstract description 2
- 239000007858 starting material Substances 0.000 abstract description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- -1 methyl- Chemical group 0.000 description 3
- 238000000967 suction filtration Methods 0.000 description 3
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 2
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 238000002485 combustion reaction Methods 0.000 description 2
- 239000003546 flue gas Substances 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- 230000004075 alteration Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000013068 control sample Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 125000004309 pyranyl group Chemical class O1C(C=CC=C1)* 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 230000001953 sensory effect Effects 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Saccharide Compounds (AREA)
Abstract
The invention belongs to the technical field of organic synthesis, and particularly relates to a preparation method and application of 3, 6-dehydration-D-glucopyranose, wherein the preparation method takes methyl-alpha-D-glucopyranose as a starting material, and the 3, 6-dehydration-D-glucopyranose is synthesized through three-step reaction. The fragrant raw material can be added into cigarettes to increase the sweet feeling of the oral cavity, enrich the fragrance of the cigarettes, increase the permeability and fineness of the smoke, improve the comfort of the aftertaste and have potential application value.
Description
Technical Field
The invention belongs to the technical field of organic synthesis, and particularly relates to a preparation method of 3, 6-dehydrated-D-glucopyranose and application of the 3, 6-dehydrated-D-glucopyranose serving as a sweet raw material in cigarettes.
Background
3, 6-Dehydrated-D-glucopyranose belongs to pyran compounds generated by sugar degradation, and has the characteristics of volatility, fat solubility, water solubility and the like. The preparation method of the 3, 6-dehydration-D-glucopyranose which is commercially available at present is to collect cellulose combustion flue gas and purify the cellulose combustion flue gas by adopting a column chromatography method, so that the preparation cost is extremely high. However, no synthesis studies of 3, 6-anhydro-D-glucopyranose have been reported so far, and thus, development of a synthesis study of 3, 6-anhydro-D-glucopyranose is of great importance.
Disclosure of Invention
The invention aims to provide a preparation method of 3, 6-dehydrated-D-glucopyranose, which is simple to operate, high in yield and easy to produce in a large scale, and an application of the preparation method serving as a special tobacco sweet flavor raw material in cigarettes, so as to solve the problem of high preparation cost of the existing 3, 6-dehydrated-D-glucopyranose.
In order to achieve the above purpose, the application is realized by the following technical scheme:
a preparation method of 3, 6-dehydrated-D-glucopyranose comprises the following steps:
Step 1, preparing an intermediate compound (II): sequentially adding raw materials of methyl-alpha-D-glucopyranoside (I), a sulfonylation reagent, alkali and a solvent into a reaction bottle, stirring and reacting for 5-10 hours at 50-100 ℃, adding a saturated sodium chloride solution for washing after the reaction is finished, extracting and separating to obtain an organic phase, drying the organic phase by using anhydrous Na 2SO4, and evaporating the solvent under reduced pressure to obtain an intermediate compound (II);
Step 2, intermediate compound (III) preparation: sequentially adding an intermediate compound (II), a catalyst and a solvent into a reaction bottle, reacting for 4-8 hours at 40-80 ℃, filtering after the reaction is finished, and concentrating the filtrate under reduced pressure to obtain an intermediate compound (III);
step 3, preparing a target product (IV): sequentially adding an intermediate compound (III), a catalyst and a solvent into a reaction bottle, reacting for 2-8 hours at 20-50 ℃ in a hydrogen atmosphere, evaporating the solvent under reduced pressure after the reaction is finished, and separating a crude product by silica gel column chromatography to obtain a target product 3, 6-dehydration-D-glucopyranose (IV).
Preferably, in the step 1, the sulfonylating agent is one of methanesulfonyl chloride, trifluoromethanesulfonyl chloride, benzenesulfonyl chloride, p-toluenesulfonyl chloride or p-nitrobenzenesulfonyl chloride; the alkali is one of potassium carbonate, triethylamine or pyridine; the solvent is one of acetonitrile, dichloromethane or tetrahydrofuran.
Preferably, the molar ratio of the methyl-alpha-D-glucopyranoside (I) to the sulfonylating agent is 1: (1.0-1.5).
Preferably, in the step 2, the catalyst is one of ferric triflate, ferric trichloride or ferric tribromide; the solvent is one of acetonitrile, methanol or tetrahydrofuran.
Preferably, the molar ratio of the intermediate compound (II) to the catalyst is 1: (0.1-2).
Preferably, in the step 3, the catalyst is one of palladium carbon, raney nickel or zinc powder; the solvent is one of acetonitrile, dichloromethane or tetrahydrofuran.
Preferably, the mass ratio of the intermediate compound (III) to the catalyst is 1: (0.05-1).
An application of the 3, 6-dehydrated-D-glucopyranose prepared by any one of the above materials, which is used as a sweet flavor raw material for cigarettes and is applied to cigarettes.
Preferably, the addition amount of the 3, 6-dehydrated-D-glucopyranose serving as a sweet flavor raw material for cigarettes is 1-100 ppm of the mass of tobacco shreds.
The beneficial effects of the invention are as follows:
according to the technical scheme, the methyl-alpha-D-glucopyranoside is used as a starting material, 3, 6-dehydrated-D-glucopyranoside is synthesized through three-step reaction, and compared with the synthesis method reported in the existing literature, the method disclosed by the invention adopts a more accurate hydroxyl protection strategy, is simpler in process, has high utilization rate of reaction atoms, has the total yield of the three-step reaction of more than 60%, is suitable for large-scale production, and has a wide application prospect. The fragrant raw material can be added into cigarettes to increase the sweet feeling of the oral cavity, enrich the fragrance of the cigarettes, increase the permeability and fineness of the smoke, improve the comfort of the aftertaste and have potential application value.
Detailed Description
The following examples are given by way of illustration only and are not to be construed as limiting the scope of the invention.
The application relates to a preparation method of 3, 6-dehydrated-D-glucopyranose, which comprises the following preparation steps:
In the technical scheme of the application, reagents, instruments and the like are obtained through normal commercial paths unless explicitly stated otherwise.
Example 1
A preparation method of 3, 6-dehydrated-D-glucopyranose comprises the following preparation steps:
Step 1, preparing an intermediate compound (II): in a 100mL round bottom flask, 1.94g (10 mmol) of methyl-. Alpha. -D-glucopyranoside, 1.85g (11 mmol) of trifluoromethanesulfonyl chloride, 11.1g (11 mmol) of triethylamine and 20mL of acetonitrile were charged, and then reacted at 0℃for 2 hours. After the completion of the reaction, 20mL of a saturated sodium hydrogencarbonate solution and 20mL of a saturated sodium chloride solution were added, and the organic phase was separated by extraction and dried over anhydrous Na 2SO4, and the solvent was distilled off under reduced pressure to obtain 1.79g of intermediate compound (II) in 92.3% yield.
Step 2, intermediate compound (III) preparation: 1.79g (10 mmol) of intermediate compound (II), 2.06g (10 mmol) of ferric triflate and 20mL of acetonitrile are sequentially added into a reaction bottle to react for 8 hours at 80 ℃, after the reaction is finished, suction filtration is carried out, and the filtrate is concentrated under reduced pressure to obtain 1.50g of intermediate compound (III) with the yield of 84.0%.
Step 3, preparing a target product (IV): 1.50g (10 mmol) of intermediate compound (III), 0.59g (10 mmol) of Raney nickel and 20mL of tetrahydrofuran are sequentially added into a reaction bottle to react for 8 hours at 50 ℃, the solvent is distilled off under reduced pressure after the reaction is finished, and the crude product is separated by silica gel column chromatography to obtain 1.26g of target product 3, 6-dehydrated-D-glucopyranose (IV) with the yield of 84.0%. The total yield of the three-step reaction is 65.0%.
Example 2
A preparation method of 3, 6-dehydrated-D-glucopyranose comprises the following preparation steps:
Step 1, preparing an intermediate compound (II): in a 100mL round bottom flask, 1.94g (10 mmol) of methyl-. Alpha. -D-glucopyranoside, 2.52g (15 mmol) of trifluoromethanesulfonyl chloride, 11.1g (11 mmol) of triethylamine and 20mL of acetonitrile were charged, and then reacted at 0℃for 2 hours. After the completion of the reaction, 20mL of a saturated sodium hydrogencarbonate solution and 20mL of a saturated sodium chloride solution were added to wash, and the organic phase was separated by extraction and dried over anhydrous Na 2SO4, and the solvent was distilled off under reduced pressure to obtain 1.85g of intermediate compound (II) in 95.4% yield.
Step 2, intermediate compound (III) preparation: 1.79g (10 mmol) of intermediate compound (II), 3.09g (15 mmol) of ferric triflate and 20mL of acetonitrile are sequentially added into a reaction bottle to react for 8 hours at 80 ℃, after the reaction is finished, suction filtration is carried out, and the filtrate is concentrated under reduced pressure to obtain 1.52g of intermediate compound (III) with the yield of 84.9%.
Step 3, preparing a target product (IV): 1.50g (10 mmol) of intermediate compound (III), 0.35g (6 mmol) of Raney nickel and 20mL of tetrahydrofuran are sequentially added into a reaction bottle to react for 8 hours at 50 ℃, the solvent is distilled off under reduced pressure after the reaction is finished, and the crude product is separated by silica gel column chromatography to obtain 1.28g of target product 3, 6-dehydrated-D-glucopyranose (IV) with the yield of 85.1%. The total yield of the three-step reaction is 68.9%.
Example 3
A preparation method of 3, 6-dehydrated-D-glucopyranose comprises the following preparation steps:
Step 1, preparing an intermediate compound (II): in a 100mL round bottom flask, 1.94g (10 mmol) of methyl-. Alpha. -D-glucopyranoside, 2.29g (12 mmol) of p-toluenesulfonyl chloride, 15.2g (15 mmol) of triethylamine and 20mL of acetonitrile were added, followed by reaction at 0℃for 2 hours. After the completion of the reaction, 20mL of a saturated sodium hydrogencarbonate solution and 20mL of a saturated sodium chloride solution were added, and the organic phase was separated by extraction and dried over anhydrous Na 2SO4, and the solvent was distilled off under reduced pressure to obtain 1.79g of the intermediate compound (II) in 92.5% yield.
Step 2, intermediate compound (III) preparation: 1.79g (10 mmol) of intermediate compound (II), 3.24g (20 mmol) of ferric trichloride and 20mL of acetonitrile are sequentially added into a reaction bottle to react for 8 hours at 80 ℃, suction filtration is carried out after the reaction is finished, and the filtrate is concentrated under reduced pressure to obtain 1.52g of intermediate compound (III) with the yield of 84.7%.
Step 3, preparing a target product (IV): 1.50g (10 mmol) of intermediate compound (III), 0.59g (10 mmol) of Raney nickel and 20mL of tetrahydrofuran are sequentially added into a reaction bottle to react for 8 hours at 50 ℃, the solvent is distilled off under reduced pressure after the reaction is finished, and the crude product is separated by silica gel column chromatography to obtain 1.26g of target product 3, 6-dehydrated-D-glucopyranose (IV) with the yield of 84.0%. The total yield of the three-step reaction is 65.8 percent.
Fragrance performance test: weighing a certain amount of 3, 6-dehydrated-D-glucopyranose (IV), and diluting with ethanol to obtain 5% solution for later use. Weighing 100g of blank cigarette tobacco shreds without flavoring, uniformly spreading in a clean tray, uniformly spraying an ethanol solution of the compound IV on the tobacco shreds to obtain flavored tobacco shreds with specific gravity of 1ppm, 5ppm, 10ppm, 50ppm and 100ppm of the compound IV and the tobacco shreds, sealing and placing for 4 hours, placing into a 50 ℃ oven for drying, humidifying to standard moisture (12%), rolling into standard cigarettes, balancing moisture (humidity 60% +/-2%, temperature 22+/-1 ℃) for 48 hours, and then evaluating. The control sample is a blank cigarette and is balanced for 48 hours under the same temperature and humidity conditions.
Table 1 sensory evaluation results
As can be seen from table 1: the 3, 6-dehydrated-D-glucopyranose has the functions of obviously improving and modifying the aroma of cigarettes, reducing the irritation, improving the taste and keeping the aftertaste clean and comfortable. The cigarette has outstanding sweet taste, obviously improves the sweet return characteristic of the cigarette smoke, and has obvious sweet and moist taste characteristics of the cigarette, and the recommended dosage is as follows: 1-100ppm.
Although embodiments of the present invention have been shown and described, it will be understood by those skilled in the art that various changes, modifications, substitutions and alterations can be made therein without departing from the spirit and scope of the invention as defined by the appended claims and their equivalents.
Claims (9)
1. A preparation method of 3, 6-dehydrated-D-glucopyranose is characterized by comprising the following steps:
Step 1, preparing an intermediate compound (II): sequentially adding raw materials of methyl-alpha-D-glucopyranoside (I), a sulfonylation reagent, alkali and a solvent into a reaction bottle, stirring and reacting for 5-10 hours at 50-100 ℃, adding a saturated sodium chloride solution for washing after the reaction is finished, extracting and separating to obtain an organic phase, drying the organic phase by using anhydrous Na 2SO4, and evaporating the solvent under reduced pressure to obtain an intermediate compound (I I);
Step 2, intermediate compound (III) preparation: sequentially adding an intermediate compound (II), a catalyst and a solvent into a reaction bottle, reacting for 4-8 hours at 40-80 ℃, filtering after the reaction is finished, and concentrating the filtrate under reduced pressure to obtain an intermediate compound (III);
step 3, preparing a target product (IV): sequentially adding an intermediate compound (III), a catalyst and a solvent into a reaction bottle, reacting for 2-8 hours at 20-50 ℃ in a hydrogen atmosphere, evaporating the solvent under reduced pressure after the reaction is finished, and separating a crude product by silica gel column chromatography to obtain a target product 3, 6-dehydration-D-glucopyranose (IV).
2. The method for preparing 3, 6-anhydro-D-glucopyranose according to claim 1, wherein in step 1, the sulfonylating agent is one of methanesulfonyl chloride, trifluoromethanesulfonyl chloride, benzenesulfonyl chloride, p-toluenesulfonyl chloride or p-nitrobenzenesulfonyl chloride; the alkali is one of potassium carbonate, triethylamine or pyridine; the solvent is one of acetonitrile, dichloromethane or tetrahydrofuran.
3. The method for producing 3, 6-anhydro-D-glucopyranose according to claim 1, wherein the molar ratio of the methyl- α -D-glucopyranoside (I) to the sulfonylating agent is 1:1 (1.0 to 1.5).
4. The method for preparing 3, 6-dehydrated-D-glucopyranose according to claim 1, wherein in step 2, the catalyst is one of ferric triflate, ferric trichloride or ferric tribromide; the solvent is one of acetonitrile, methanol or tetrahydrofuran.
5. The method for producing 3, 6-anhydro-D-glucopyranose according to claim 1, wherein the molar ratio of the intermediate compound (II) to the catalyst is 1: (0.1-2).
6. The method for preparing 3, 6-dehydrated-D-glucopyranose according to claim 1, wherein in step 3, the catalyst is one of palladium carbon, raney nickel or zinc powder; the solvent is one of acetonitrile, dichloromethane or tetrahydrofuran.
7. The method for producing 3, 6-anhydro-D-glucopyranose according to claim 1, wherein the mass ratio of the intermediate compound (III) to the catalyst is 1: (0.05-1).
8. Use of 3, 6-anhydro-D-glucopyranose, prepared according to any of the preceding claims 1 to 7, as a raw material for a sweet taste for cigarettes in cigarettes.
9. The use according to claim 8, characterized in that 3, 6-anhydro-D-glucopyranose is added as a raw material for tobacco sweet flavor in an amount of 1 to 100ppm based on the mass of tobacco shreds.
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| CN202410031348.0A CN117924376A (en) | 2024-01-09 | 2024-01-09 | Preparation method and application of 3, 6-dehydrated-D-glucopyranose |
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| CN202410031348.0A CN117924376A (en) | 2024-01-09 | 2024-01-09 | Preparation method and application of 3, 6-dehydrated-D-glucopyranose |
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| CN117924376A true CN117924376A (en) | 2024-04-26 |
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| CN202410031348.0A Pending CN117924376A (en) | 2024-01-09 | 2024-01-09 | Preparation method and application of 3, 6-dehydrated-D-glucopyranose |
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