Preparation method of 2-deoxy-D-glucose

A technology of glucose and glucosene, which is applied in the field of preparation of 2-deoxy-D-glucose, can solve the problems of no production value, expensive reaction reagents, difficult purification, etc., and achieve the effect of easy product purification, convenient operation, and easy industrialization

Active Publication Date: 2013-02-13
SHANDONG LUKANG SHELILE PHARMA
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The synthesis method patented in 2004 (PCT Int.Appl., 2004058786, 15 Jul 2004), is to obtain 2-deoxy-D-glucose through three steps starting from glucosene, which is cumbersome and costly
Chinese patent CN 102180914A has improved the above-mentioned patents. The product is obtained from triacetylglucosene through a two-step reactio

Method used

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  • Preparation method of 2-deoxy-D-glucose

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Embodiment 1

[0027] A. Preparation of 3,4,6-tri-O-benzylglucoene (intermediate 1)

[0028] Potassium carbonate (50 g, 0.362 mol) was added to a solution of 3,4,6-triacetylglucosene (55 g, 0.202 mol) in methanol (400 ml), and the reaction mixture was stirred overnight at room temperature. After filtering off inorganic salts, the filtrate was evaporated to dryness. Add DMF (400ml) and cool to 0°C, add sodium hydride (40g, 60% content, 1.000mol) in batches, stir for 30min, add benzyl bromide (125.7g, 0.735mol) dropwise, remove the ice bath after the addition, The reaction mixture was stirred at room temperature until the reaction was complete, followed by TLC detection. The mixture was cooled to 0°C, ice water (1000ml) was added slowly followed by dichloromethane (800ml), the organic layer was separated and the aqueous solution was extracted with dichloromethane (2x300ml). The combined organic phases were washed with water until neutral, then with brine, and dried over anhydrous sodium sulf...

Embodiment 2

[0040] A. Preparation of 3,4,6-tri-O-benzylglucoene (intermediate 1)

[0041] Sodium hydroxide (8.4g, 0.210mol) was added to a solution of 3,4,6-triacetylglucosene (55g, 0.202mol) in methanol (400ml), and the reaction mixture was stirred at room temperature overnight. After filtering off inorganic salts, the filtrate was concentrated to dryness under reduced pressure. Add DMF (400ml) and cool to 0°C, add sodium hydride (40g, 60% content, 1.000mol) in batches, stir for 30min, add benzyl bromide (125.7g, 0.735mol) dropwise, remove the ice bath after the addition, The reaction mixture was stirred at room temperature until the reaction was complete, followed by TLC detection. The mixture was cooled to 0°C, ice water (1000ml) was added slowly followed by dichloromethane (800ml), the organic layer was separated and the aqueous solution was extracted with dichloromethane (2x300ml). The combined organic phases were washed with water until neutral, then with brine, and dried over anh...

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Abstract

The invention discloses a preparation method of 2-deoxy-D-glucose, relating to the field of production of active pharmaceutical ingredients. The preparation method comprises the following steps of: a, taking 3, 4, 6-triacetyl glucose alkenes as raw materials, removing acetyl protection groups in the presence of alkalis and then performing benzyl protection to obtain an intermediate I shown as a formula II; b, acid-hydrolyzing the intermediate I obtained in the step a to obtain an intermediate II shown as a formula III; and c, performing hydrogenolysis on the intermediate II obtained in the step b to de-protect and re-crystallizing to obtain the 2-deoxy-D-glucoses shown as a formula I. Compared with the prior art, the preparation method of the 2-deoxy-D-glucoses has the advantages of simple preparation process, easy purification for products, high yield, low cost and the like, and is more beneficial to achieving large-scale industrial production.

Description

technical field [0001] The invention relates to the field of raw material medicine production, in particular to a preparation method of 2-deoxy-D-glucose. Background technique [0002] Deoxyglucose is a large family of glucose derivatives. Deoxyglucose is ubiquitous in various microorganisms, especially bacteria and actinomycetes, and plays an important regulatory role in the metabolism of actinomycetes and bacteria. The most used in production practice is 2-deoxy-D-glucose (2-Dexoy-D-Glucose, abbreviated: 2-DG), which is a natural anti-metabolite antibiotic (Woodward, 1954, Cancer Res .14:599-605), which can inhibit virus infection, yeast fermentation, pathogenic bacteria and tumor cell growth and other physiological and pharmacological effects. It has antiviral, antibacterial, anticancer, antiepileptic and other effects, and is used to prevent viral and pathogenic bacteria infections, etc., and can prevent HSV, HIV, SARS, influenza virus, etc. and infectious diseases caus...

Claims

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Application Information

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IPC IPC(8): C07H3/08C07H1/00
CPCY02P20/55
Inventor 李传宾郭强董坤彭欣
Owner SHANDONG LUKANG SHELILE PHARMA
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