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A 2-o-(2,3,4,6-tetra-o-acetyl-β-d-glucopyranosyl)-3-o-benzyl-5,6-o-isopropylidene- The preparation method of antacid

A technology of glucopyranosyl and isopropylidene, which is applied in the preparation of sugar derivatives, chemical instruments and methods, sugar derivatives, etc., can solve the problems of high production cost, harsh reaction conditions, and complicated synthesis process, and achieve the goal of reaction The process is easy to control, the reaction conditions are mild, and the reaction yield is high

Active Publication Date: 2017-05-24
SHANDONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In this preparation method, 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-2,2,2-trichloroethyl carbonate is trichloroethyl chloroformate and 2, 3,4,6-Tetra-O-acetyl-β-D-glucose is prepared by reaction, the reaction conditions are harsh, trichloroethyl chloroformate is expensive, phosgene is used in the synthesis process, the toxicity is high, the synthesis process is complicated, and the production cost high

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Add 3.52g vitamin C, 2.76g p-toluenesulfonic acid, and 15mL acetone to a 100mL single-necked flask, react in an ice bath for 4h, vacuum filter, wash the filter cake with ethyl acetate, and vacuum dry to obtain 5,6-O -Isopropylidene-L-ascorbic acid is 4.08 g of white solid, and the yield is 94.4%.

[0019] Add 2.16g of 5,6-O-isopropylidene-L-ascorbic acid, 1.06g of sodium carbonate, 1.20mL of benzyl bromide, acetone 20mL, reacted under reflux for 4h, after the above solution was lowered to room temperature, the reaction solution was washed with water, extracted with ethyl acetate (3×20mL), washed with saturated sodium chloride solution, dried with anhydrous magnesium sulfate, filtered, evaporated under normal pressure In addition to ethyl acetate, purified by column chromatography (petroleum ether: ethyl acetate = 3:1) to obtain bright yellow oil, that is, 3-O-benzyl-5,6-O-isopropylidene-L-anti Blood acid 1.89g, the yield is 61.8%.

[0020] Add 3.09g (7.5mmol) 2,3,4,6-...

Embodiment 2

[0023] Add 3.52g of vitamin C, 2.76g of p-toluenesulfonic acid, and 15mL of acetone into a 100mL single-necked flask, react in an ice bath for 4h, vacuum filter, wash the filter cake with ethyl acetate, and dry in vacuo to obtain 5,6-O -Isopropylidene-L-ascorbic acid is 4.08 g of white solid, and the yield is 94.4%.

[0024] Add 2.16 g of 5,6-O-isopropylidene-L-ascorbic acid, 1.40 g of potassium carbonate, 1.20 mL of benzyl bromide, and 20mL, reacted under reflux for 4h, after the above solution dropped to room temperature, the reaction solution was washed with water, extracted with ethyl acetate (3×20mL), washed with saturated sodium chloride solution, dried with anhydrous magnesium sulfate, filtered, and Ethyl acetate was removed by pressure evaporation, and purified by column chromatography (petroleum ether: ethyl acetate = 3:1) to obtain a bright yellow oil, namely 3-O-benzyl-5,6-O-isopropylidene-L -Ascorbic acid 1.43g, the yield is 46.7%.

[0025]Add 4.94g (12mmol) 2,3,...

Embodiment 3

[0027] The preparations of 5,6-O-isopropylidene-L-ascorbic acid and 3-O-benzyl-5,6-O-isopropylidene-L-ascorbic acid are the same as in Example 1.

[0028] Add 3.09g (7.5mmol) 2,3,4,6-tetra-O-acetyl-α-bromo Glucose substitute, 10mL 5wt% sodium hydroxide solution, 1.82g (8mmol) benzyltriethylammonium chloride, 1.84g (6mmol) 3-O-benzyl-5,6-O-isopropylidene-L -Ascorbic acid was dissolved in 30mL of dichloromethane and added dropwise to the above solution. During the reaction, the temperature of the reaction was controlled to be 35°C, and the reaction time was 4h. Extracted, dried over anhydrous sodium sulfate, filtered, dichloromethane was evaporated under normal pressure, and purified by column chromatography (petroleum ether: ethyl acetate = 2:1) to obtain the product 2-O-(2,3,4,6-tetra -O-acetyl-β-D-glucopyranosyl)-3-O-benzyl-5,6-O-isopropylidene-ascorbic acid 2.61 g, yield 68.7%.

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PUM

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Abstract

The invention relates to a preparation method of 2-O-(2, 3, 4, 6-tetra-O-acetyl-Beta-D-glucopyranosyl)-3-O-benzyl-5, 6-isopropylidene-ascorbic acid. The preparation method includes: under catalysis of p-toluenesulfonic acid and under the condition of ice bath, allowing vitamin C and acetone to react for 3-5h, and performing filtering, washing and drying to obtain white solid of 5, 6-O-isopropylidene-L-ascorbic acid; adding mixture of benzyl bromide, alkali and the white solid of the 5, 6-O-isopropylidene-L-ascorbic acid into solvent, performing heating to allow reflux reaction for 3-5h, and washing and purifying reaction liquid to obtain 3-O-benzyl-5, 6-O-isopropylidene-L-ascorbic acid; dissolving the 3-O-benzyl-5, 6-O-isopropylidene-L-ascorbic acid with dichloromethane, dropwise adding dissolved solution into sodium hydroxide solution containing phase-transfer catalysts such as 2, 3, 4, 6-tetra-O-acetyl-Alpha-glucopyranosyl bromide and quaternary ammonium salts, and allowing reaction to obtain a product. The preparation method has the advantages that raw materials are easy to obtain, reaction conditions are moderate, the synthetic process is easy to control, yield is high, and the method has important applicable value.

Description

technical field [0001] The present invention relates to the preparation of a vitamin C derivative, in particular to a 2-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-3-O- The preparation method of benzyl-5,6-O-isopropylidene-ascorbic acid belongs to the technical field of chemical synthesis. Background technique [0002] Vitamin C, also known as L-ascorbic acid, has the molecular formula C 6 h 8 o 6 , although the required amount is small, it is an essential nutrient element to maintain the body. It is a class of low-molecular organic compounds necessary to maintain the normal life activities of organisms. It plays an irreplaceable role in the protection of human health and the growth of animals. Vitamin C has many important functions and uses: it is used for medical care, preventing the occurrence of various chronic infectious diseases, scurvy, etc., enhancing resistance, promoting the healing of body wounds, and serving as an auxiliary drug in treatment and health care ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H1/00C07H17/04
Inventor 张志德李雪娇陈玉琴
Owner SHANDONG NORMAL UNIV