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Bromotetraacetylglucose, synthetic method and use thereof

A bromotetraacetyl and pentaacetylglucose technology, applied in chemical instruments and methods, sugar derivatives, sugar derivatives, etc., can solve problems such as troublesome operation and inability to accurately weigh the amount of hydrogen bromide gas added, and achieve product High yield, simple and efficient method

Active Publication Date: 2010-03-17
YANCHENG CITY CHUNZHU AROMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0021] Guo Cancheng introduced dry hydrogen bromide gas under ice bath cooling. This step is not only cumbersome to operate, but also the reaction solvent must be dry, and the amount of hydrogen bromide gas added cannot be accurately weighed.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0077] 1. Synthesis of Pentaacetylglucose

[0078] Add 400 g of glucose monohydrate and 1500 g of acetic anhydride into a 2 L three-necked flask, and stir and mix in an ice-water bath. Add 0.001g of concentrated sulfuric acid dropwise to the mixed solution for 2 times, remove the ice-water bath when the reaction flask no longer generates heat, and heat and reflux in the water bath for 2 hours to complete the reaction. The reaction solution is analyzed by high performance liquid chromatography to contain 273g of pentaacetyl Glucose, the solution can be directly used in the next step without treatment.

[0079] 2. Synthesis of tetraacetylbromoglucose

[0080] Under nitrogen protection and stirring, add the solution containing 273g of pentaacetylglucose, 600g of glacial acetic acid, and 600g of methylene chloride obtained in the above steps to a 2L three-necked flask, add 67g of phosphorus tribromide, and stir for 10 minutes to mix the reaction solution Evenly, then add 40g of ...

Embodiment 2

[0084] This embodiment is carried out in the same manner as in Example 1, except that the pentaacetylglucose solution prepared in Example 1 is removed with a rotary evaporator at a pressure of 0.02 bar to remove the remaining acetic anhydride and the acetic acid generated, and then pour the residual solution into A large amount of ice water was poured into 1000 g of diethyl ether under stirring, and the stirring was continued for 0.5 hours. Then, suction filtration was carried out under a pressure of 0.02 bar, and a white solid was obtained by washing with water for 5 times, and dried in vacuo to obtain 538 g of pentaacetylglucose as a white powdery solid. This solid product was further used to prepare 235 g of tetraacetylglucose bromide.

[0085] The tetraacetylbromoglucose content measured by high performance liquid chromatography is 99.5%.

Embodiment 3

[0087] This embodiment was carried out in the same manner as in Example 1, except that 410 g of glucose monohydrate and 3800 g of acetic anhydride were used to prepare 240 g of tetraacetylbromoglucose.

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PUM

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Abstract

The invention relates to a synthetic method of bromotetraacetylglucose, bromotetraacetylglucose and use thereof. The invention comprises the steps of taking glucose as raw materials, carrying out acetylation reaction by acetyl oxide as an acylating agent, then carrying out bromination reaction by phosphorous tribromide and hydrobromic acid as a brominating agent, and then carrying out recrystallization by diethyl, and at last obtaining bromotetraacetylglucose. The invention has the advantages of simple and efficient method, high yield and high purity reaching above 98.9%.

Description

【Technical field】 [0001] The invention relates to the technical field of organic compound synthesis. More specifically, the present invention relates to a synthesis method of bromotetraacetylglucose, the bromotetraacetylglucose and its application. 【Background technique】 [0002] Glucose is an important monosaccharide closely related to life in nature, and it can directly participate in the metabolic process in the human body. Glucose is easier to absorb than any other monosaccharide in the digestive tract, and it can be directly used by human tissues after absorption. It can replenish water and sugar in the body, and has the functions of replenishing body fluids, supplying energy, replenishing blood sugar, strengthening the heart and diuresis, and detoxifying. Glucose has no side effects except for diabetics. It can be used directly in the food and pharmaceutical industries. Sugar esters are essential nutrients for human survival and have a wide range of physiological a...

Claims

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Application Information

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IPC IPC(8): C07H13/06C07H1/00
Inventor 蒋思翠何林美伍阳罗昌荣
Owner YANCHENG CITY CHUNZHU AROMA
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