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2-deoxy-D-glucose preparation method

A technology of glucose and precursor, applied in the field of organic compound preparation, can solve the problems of complex process, high cost, low yield, etc., and achieve the effects of simple synthesis process, low production cost, and low requirements for production equipment

Inactive Publication Date: 2014-08-13
GUANGZHOU TANKE BIO TECH +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] There are many studies on the chemical synthesis of 2-deoxy-D-glucose, but most of the current synthetic methods involve hydroxyl protection and catalytic hydrogenation, which are not only time-consuming, complex process, high cost, and low yield, so the market price is as high as 20,000 yuan / kg

Method used

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preparation example Construction

[0023] A preparation method of 2-deoxy-D-glucose, comprising the following steps:

[0024] (1) Heat and hydrolyze chitin with excess concentrated hydrochloric acid for 2 to 4 hours, decolorize, filter until the filtrate is colorless, concentrate the filtrate, wash, and dry to obtain the precursor;

[0025] (2) Mix the precursor obtained in step (1) with H 2 SO 4 -SiO 2 Mix solid acid catalyst and excess methanol, heat and reflux for 7 to 9 hours, add an appropriate amount of calcium chloride, neutralize the reaction solution, filter to obtain a white solid;

[0026] (3) Dissolve the white solid obtained in step (2) in excess dilute hydrochloric acid, add an appropriate amount of sodium nitrite, react for 0.5 to 1.5 hours, neutralize the reaction solution, crystallize, filter, and concentrate the filtrate to obtain a crude product;

[0027] (4) Recrystallize the crude product and dry it to obtain crystalline 2-deoxy-D-glucose.

[0028] Preferably, in step (1), the mass volu...

Embodiment 1

[0039] (1) Mix 100g of chitin with 600ml of 31% concentrated hydrochloric acid, heat and hydrolyze for 4 hours, decolorize, filter until the filtrate is colorless, concentrate the filtrate, wash, and dry to obtain 61.2g of the precursor;

[0040] (2) Mix the precursor obtained in step (1) with 30.6gH 2 SO 4 -SiO 2 Mix the solid acid catalyst and 918ml of methanol, heat and reflux for 7 hours, add 30.6g of calcium chloride, then neutralize the reaction solution with alkali, filter, and recover the solvent from the filtrate to obtain 52.4g of white solid;

[0041] (3) Dissolve the white solid obtained in step (2) in 2358ml of 5% dilute hydrochloric acid, add 29.1g of sodium nitrite, react at 30°C for 0.5 hours, neutralize, concentrate the reaction solution, crystallize, filter to remove sodium chloride, and concentrate the filtrate , 30.2g crude product was obtained;

[0042] (4) Recrystallize the crude product with methanol and acetone at a ratio of 1:1.5, and dry to obtain ...

Embodiment 2

[0045] A preparation method of 2-deoxy-D-glucose, comprising the steps of:

[0046] (1) Mix 100g of chitin with 500ml of 34% concentrated hydrochloric acid, heat and hydrolyze for 3 hours, decolorize, filter until the filtrate is colorless, concentrate the filtrate, wash, and dry to obtain 62.2g of the precursor;

[0047] (2) Mix the precursor obtained in step (1) with 24.9gH 2 SO 4 -SiO 2 Mix the solid acid catalyst and 1100ml of methanol, heat and reflux for 8 hours, add 24.9g of calcium chloride, then neutralize the reaction solution with alkali, filter, and recover the solvent from the filtrate to obtain 53.0g of white solid;

[0048] (3) Dissolve the white solid obtained in step (2) in 1600ml of 10% dilute hydrochloric acid, add 27.9g of sodium nitrite, react at 20°C for 1 hour, neutralize, concentrate the reaction solution, crystallize, filter to remove sodium chloride, and concentrate the filtrate , to obtain crude product 29.6g;

[0049] (4) Recrystallize the crude...

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Abstract

The invention discloses a preparation method of 2-deoxy-D-glucose, which comprises the following steps: taking chitin as an initial raw material, preparing a precursor, then employing solid acid H2SO4-SiO2 as a catalyst, reacting 2-amino-D-glucose hydrochloride and methanol, then reacting with sodium nitrite and hydrochloric acid, forming a nitroso compound and performing intramolecular rearrangement, removing amino, and finally preparing the 2-deoxy-D-glucose. According to the preparation method, hydroxy protection and catalysis hydrogenation are not required, time consuming is short, the synthesis technology is simple, the production equipment requirement is low, the production cost is low, product quality is stable, and the preparation method is adapted to industrial production.

Description

technical field [0001] The invention belongs to the technical field of organic compound preparation, and in particular relates to a preparation method of 2-deoxy-D-glucose which is antiviral, antibacterial and prevents influenza virus. Background technique [0002] 2-Deoxy-D-glucose is a natural anti-metabolite antibiotic, which has various physiological and pharmacological effects such as inhibiting virus infection, yeast fermentation, bacteria and tumor cell growth, etc. Widely used in basic research. In practice, it is used to prevent virus and pathogen infection, such as HSV, HIV, SARS, influenza virus and other infectious diseases caused by pathogenic bacteria. Its antiviral and antibacterial effects are due to its structure similar to 2-deoxy-D-ribose, which can interfere with bacteria Utilization of 2-deoxy-D-ribose by an enzyme system. In addition, it is also an important pharmaceutical intermediate, which is widely used in pharmaceutical and cosmetic industries. I...

Claims

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Application Information

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IPC IPC(8): C07H3/08C07H1/00
Inventor 舒绪刚许祥段静娜付志欢樊明智高均勇
Owner GUANGZHOU TANKE BIO TECH