Method for preparing 2-deoxy-D-glucose

A technology of glucose and glucosamine hydrochloride, applied in the field of sugar chemistry, can solve the problems of complex process, low yield, high cost, etc., and achieve the effect of cheap and easy-to-obtain raw materials, fewer operation steps, and low cost

Active Publication Date: 2017-03-15
JINAN SAMUEL PHARM CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In order to solve the problems of complex process, low yield and high cost in the existing 2-deoxy-D-glucose synthesis technology, the invention provides a preparation method of 2-deoxy-D-glucose

Method used

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  • Method for preparing 2-deoxy-D-glucose

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preparation example Construction

[0042] A preparation method of 2-deoxy-D-glucose, comprising the following steps:

[0043] ①Add glucosamine hydrochloride into water, stir to dissolve it, then add sodium hydroxide to it, stir evenly to obtain mixed solution 1, add p-anisaldehyde dropwise to mixed solution 1, and keep mixed solution 1 during the dropping process The temperature is 2~7°C, and the reaction is stirred at this temperature for 10~15 hours to obtain the reaction solution 1, and methyl tert-butyl ether is added to the reaction solution 1, stirred for 20~40 minutes, and suction filtered to obtain the filter cake 1 is 2-(4'-methoxybenzylidene)amino-2-deoxy-D-glucose, spare;

[0044] The mass volume ratio of the glucosamine hydrochloride, water, sodium hydroxide, p-anisaldehyde and methyl tert-butyl ether is 20~25g: 120~150ml: 4~4.5g: 10~15g: 180~200ml ;

[0045] ②Add 2-(4'-methoxybenzylidene)amino-2-deoxy-D-glucose obtained in step ① into pyridine to dissolve to obtain mixed solution 2, add acetic an...

Embodiment 1

[0084] A preparation method of 2-deoxy-D-glucose, comprising the following steps:

[0085] ① Add 40kg of glucosamine hydrochloride into 300L of water, stir to dissolve it, then add 8kg of sodium hydroxide to it, stir well to obtain mixed solution 1, add 20kg of p-anisaldehyde dropwise to mixed solution 1, during the dropwise addition process Keep the temperature of the mixed solution 1 at 2~7°C, and stir and react at this temperature for 10 hours to obtain the reaction solution 1, add 360L methyl tert-butyl ether to the reaction solution 1, stir for 20 minutes, and suction filter, the obtained solution is filtered Cake 1 is 2-(4'-methoxybenzylidene)amino-2-deoxy-D-glucose with a yield of 94%;

[0086] ②Take 20kg of 2-(4'-methoxybenzylidene)amino-2-deoxy-D-glucose obtained in step ① and add it to 65L pyridine to dissolve to obtain the mixed solution 2, and add 40kg of acetic anhydride to the mixed solution 2 dropwise , keep the temperature of the mixed solution 2 at 0~5°C duri...

Embodiment 2

[0092] A preparation method of 2-deoxy-D-glucose, comprising the following steps:

[0093] ① Add 100kg of glucosamine hydrochloride into 480L of water, stir to dissolve it, then add 18kg of sodium hydroxide to it, stir well to obtain mixed solution 1, add 60kg of p-anisaldehyde dropwise to mixed solution 1, during the dropping process Keep the temperature of the mixed solution 1 at 2~7°C, and stir the reaction at this temperature for 10~15 hours to obtain the reaction solution 1, add 800L methyl tert-butyl ether to the reaction solution 1, stir for 20~40 minutes, pump filter, and the resulting filter cake 1 is 2-(4'-methoxybenzylidene)amino-2-deoxy-D-glucose, with a yield of 95%;

[0094] ②Dissolve 50kg of 2-(4'-methoxybenzylidene)amino-2-deoxy-D-glucose obtained in step ① into 150L pyridine to obtain mixed solution 2, and add 100kg acetic anhydride to mixed solution 2 dropwise , keep the temperature of the mixed solution 2 at 0~5°C during the dropwise addition, then add 0.5k...

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Abstract

The invention discloses a method for preparing 2-deoxy-D-glucose. According to the method, D-glucosamine which is low in price and easy to obtain serves as a starting material, p-anisaldehyde is used for protecting amino, pyridine serves as a solvent under catalysis of 4-dimethylaminopyridine (DMAP), acetic anhydride serves as a reactant for acetylation protection of all hydroxyl groups on D-glucosamine, protecting groups on the amino are removed under the acidic condition to obtain 1,3,4,6-tetra-o-acetyl-2-glucosamine hydrochloride, and the amino is further converted into isothiocyano with PhOC(=S)Cl; AIBN serves as an initiator, a free radical reaction is conducted by means of tris(trimethylsilyl)silane (TTMS-H) and 1,3,4,6-tetra-o-acetyl-2-glucosamine hydrochloride, and finally acetyl is removed to obtain 2-deoxy-D-glucose. According to the novel synthetic route, raw materials are easy to obtain, operation is easy, no chromatographic column separation is involved, the total yield is high, cost is low, and the method is suitable for large-scale production. The preparation method is simple in product aftertreatment, the product is easy to separate, and large-scale production is easy to achieve.

Description

technical field [0001] The invention relates to the technical field of sugar chemistry, in particular to a preparation method of 2-deoxy-D-glucose. Background technique [0002] 2-Deoxy-D-glucose, also known as 2-deoxyglucose, is a natural anti-metabolite antibiotic with a variety of physiological and pharmacological effects. In addition, it is also an important pharmaceutical intermediate and has a wide range of applications in pharmaceutical and cosmetic industries. application, but the current price on the market is relatively high, generally at 250-290g / yuan, which limits its application, which is mainly determined by the current preparation process. [0003] At present, there are two kinds of preparation techniques for 2-deoxy-D-glucose: one is to use glucose as a raw material to obtain 3,4,6-tri-acetyl-D-glucal through acetylation, bromination, and reduction, and then pass The preparation of 2-deoxyglucose by changing the protective group, addition, and catalytic hydr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H3/08C07H1/00
CPCY02P20/55C07H3/08C07H1/00
Inventor 李文举贾元雪唐鹏飞李秀珍
Owner JINAN SAMUEL PHARM CO LTD
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