Method for preparing tetrabenzyl pyran type hexose

A technology of tetrabenzylpyran-type and six-carbon sugar, which is applied in the preparation of sugar derivatives, chemical instruments and methods, sugar derivatives, etc., to achieve the effects of less side reactions, simplified post-treatment methods, and improved purity and yield

Active Publication Date: 2014-09-10
济南尚博医药股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The acidity of the catalyst used in this method is strong, and side reactions are prone to occur, resulting in low product purity and difficult crystallization. The subsequent treatment steps are more cumbersome, and the generated wastewater is not easy to treat and has a greater impact on the environment.
[0006] Novel catalyst-loaded solid acid has high activity, can replace inorganic liquid acid as catalyst, and is applied to the catalytic hydrolysis of sugar compounds. CN102093206A discloses a silica gel-loaded sulfuric acid Nickel-catalyzed hydrolysis of sucrose to prepare levulinic acid, the yield is 40%, silica gel-supported nickel sulfate needs high-temperature roasting, the catalyst preparation method is more complicated, and the selectivity is poor, and the yield is low

Method used

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  • Method for preparing tetrabenzyl pyran type hexose
  • Method for preparing tetrabenzyl pyran type hexose
  • Method for preparing tetrabenzyl pyran type hexose

Examples

Experimental program
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Effect test

Embodiment 1

[0038] 1) Weigh 0.1 mol of tetrabenzyl glucoside and 0.5 mol of methanol, and stir until completely mixed;

[0039] 2) Add a catalyst to the above reaction system, carry 0.01 mol of sulfuric acid-hydrofluoric acid on silica gel (based on H content), and react at 100°C for 15 hours;

[0040] 3) Filtrate, wash the filter cake with methanol, combine the filtrate and washings, concentrate under reduced pressure at 40°C to a solid, add 0.3mol of ethyl acetate, dissolve, stir and crystallize at 0°C for 5 hours, and obtain 0.086mol of tetrabenzylglucose with a purity of It was 98.3%, and the yield was 86%.

Embodiment 2

[0042] 1) Weigh 0.1 mol of tetrabenzyl glucoside and 0.8 mol of methanol, and stir until completely mixed;

[0043] 2) Add a catalyst to the above reaction system, carry 0.012mol of sulfuric acid-hydrofluoric acid on silica gel (based on H content), and react at 100°C for 18h;

[0044] 3) Filtrate, wash the filter cake with methanol, combine the filtrate and washings, concentrate under reduced pressure at 40°C to a solid, add 0.3mol of ethyl acetate, dissolve, stir and crystallize at 3°C ​​for 5 hours, and obtain 0.088mol of tetrabenzylglucose with a purity of It was 98.1%, and the yield was 88%.

Embodiment 3

[0046] 1) Weigh 0.1 mol of tetrabenzyl glucoside and 1.0 mol of methanol, and stir until completely mixed;

[0047] 2) Add a catalyst to the above reaction system, 0.015mol of sulfuric acid-hydrofluoric acid supported on silica gel (based on H content), and react at 100°C for 20h;

[0048] 3) Filtrate, wash the filter cake with methanol, combine the filtrate and washings, concentrate under reduced pressure at 40°C to a solid, add 0.3mol of ethyl acetate, dissolve, stir and crystallize at 5°C for 5 hours, and obtain 0.087mol of tetrabenzylglucose with a purity of It was 98.3%, and the yield was 87%.

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Abstract

The invention provides a method for preparing tetrabenzyl pyran type hexose, belonging to the field of sugar compounds. The method adopts a supported solid-acid catalyst namely silica gel supported sulfuric acid-hydrofluoric acid, performs catalytic hydrolysis on tetrabenzyl pyran type hexose glucoside, is simple in operation, is environment-friendly and practical, and simplifies an after-treatment method. The method comprises the steps of adding tetrabenzyl pyran type hexose glucoside and an organic solvent at room temperature, adding silica gel supported sulfuric acid-hydrofluoric acid, completing reaction, and then performing after-treatment to obtain tetrabenzyl pyran type hexose. The preparation method provided by the invention is simple in operation and easy in reaction control, reduces the cost, and is beneficial for environmental protection.

Description

technical field [0001] The invention relates to the field of sugar compounds, in particular to a method for preparing tetrabenzylpyran-type hexose. Background technique [0002] Tetrabenzylpyran six-carbon sugar, the general formula is: [0003] [0004] Including galactose, glucose, etc., glucose as an example below. [0005] In the prior art, tetrabenzylglucoside is generally adopted to prepare tetrabenzylglucose under the hydrolysis of dilute sulfuric acid and acetic acid (Kunert, Olaf; Poetschger, Irmgard; Presser, Armin; Monatshefte fur Chemie.2006,137(3 ):365-374). The acidity of the catalyst used in this method is strong, and side reactions are prone to occur, resulting in low product purity and difficult crystallization. The subsequent treatment steps are more cumbersome, and the generated wastewater is difficult to treat and has a greater impact on the environment. [0006] The new catalyst-supported solid acid has high activity, can replace inorganic liquid...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H15/18C07H1/00B01J27/12
Inventor 孟庆文赵海峰孔令华索晨苏张雷
Owner 济南尚博医药股份有限公司
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