Preparation method of 2-deoxy-D-glucose

A glucose and compound technology, applied in the field of preparation of 2-deoxy-D-glucose, can solve the problems of a large amount of strong acid wastewater, inconvenient use, difficult commercialization, etc., and achieve broad commercial application prospects. rate-enhancing effect

Active Publication Date: 2018-04-24
TIANJIN MODERN VOCATIONAL TECH COLLEGE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The above method has long reaction steps, low total reaction yield, difficult purification and difficult commercialization
[0004] In the prior art, some of the reaction conditions are strongly acidic, which is highly corrosive to equipment, and a large amount of strongly acidic wastewater is easily produced during production, causing environmental problems, and the reaction time is longer and the yield is lower.
In some technologies, the catalyst is easy to absorb moisture, difficult to store, and inconvenient to use

Method used

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  • Preparation method of 2-deoxy-D-glucose
  • Preparation method of 2-deoxy-D-glucose
  • Preparation method of 2-deoxy-D-glucose

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] A preparation method of 2-deoxy-D-glucose, comprising the following steps:

[0029] (1) To a solution of compound (III) (27.2 g, 0.1 mol) in acetonitrile (500 mL) was added CH at room temperature 3 SCH 2 Cl (3.7 g, 0.02 mol), KI (3.3 g, 0.02 mol) and water (5.4 g, 0.3 mol). After stirring at room temperature for 10 min, ethyl acetate (250 mL) and saturated sodium thiosulfate solution (150 mL) were added to the reaction solution, and the organic phase was washed with water, saturated brine, dried and concentrated under reduced pressure. The crude product was recrystallized from diethyl ether (150 mL) to obtain compound (IV) (29.2 g, white solid) with a yield of 99%.

[0030] Hydrogen NMR spectrum: (600MHz, CDCl 3 )δ5.54-5.35(m, 8H), 5.08-4.95(m, 6H), 4.37-4.19(m, 10H), 4.13(t, J=13.3Hz, 5H), 3.69(d, J=6.9Hz ,1H),3.49(s,1H),3.04(s,4H),2.42(dd,J=11.9,4.1Hz,1H),2.32-2.27(m,4H),2.14-2.00(m,45H), 1.88-1.73 (m, 5H).

[0031] (2) Dissolve compound (IV) (20 g, 0.069 mol) i...

Embodiment 2

[0036] A preparation method of 2-deoxy-D-glucose, comprising the following steps:

[0037] (1) PhCH was sequentially added to a solution of compound (V) (41.6 g, 0.1 mol) in acetonitrile (500 mL) at room temperature 2 SCH 2 Cl (1.22 g, 0.01 mol), potassium iodide (1.65 g, 0.01 mol) and water (5.4 g, 0.3 mol). After stirring at room temperature for 1 hour, ethyl acetate (250 mL) and saturated sodium thiosulfate solution (150 mL) were added to the reaction solution, and the organic phase was washed with water, saturated brine, dried and concentrated under reduced pressure. The crude product was recrystallized from diethyl ether (150 mL) to obtain compound (VI) (38.7 g, white solid) in a yield of 89%.

[0038] Hydrogen NMR spectrum: 600MHz, CDCl 3 )δ7.36-7.24(m,65H),7.17(d,J=6.0Hz,10H),5.38(s,4H),4.88(t,J=11.0Hz,5H),4.70-4.60(m,10H) ),4.57(dd,J=12.1,6.5Hz,6H),4.51(dd,J=12.1,4.6Hz,10H),4.04(dt,J=7.7,7.0Hz,9H),3.76-3.61(m, 10H), 3.61-3.54(m, 1H), 3.46-3.41(m, 4H), 3.43(dd, J=1...

Embodiment 3

[0044] A preparation method of 2-deoxy-D-glucose, comprising the following steps:

[0045] (1) To a solution of compound (III) (27.2 g, 0.1 mol) in acetonitrile (500 mL) was added n-C at room temperature 6 H 13 SCH 2 Cl (1.65 g, 0.01 mol), KI (1.65 g, 0.01 mol) and water (5.4 g, 0.3 mol). After stirring at room temperature for 1 hour, ethyl acetate (250 mL) and saturated sodium thiosulfate solution (150 mL) were added to the reaction solution, and the organic phase was washed with water, saturated brine, dried and concentrated under reduced pressure. The crude product was recrystallized from diethyl ether (150 mL) to obtain compound (IV) (25.1 g, white solid) with a yield of 85%.

[0046] Hydrogen NMR spectrum: (600MHz, CDCl 3 )δ5.54-5.35(m, 8H), 5.08-4.95(m, 6H), 4.37-4.19(m, 10H), 4.13(t, J=13.3Hz, 5H), 3.69(d, J=6.9Hz ,1H),3.49(s,1H),3.04(s,4H),2.42(dd,J=11.9,4.1Hz,1H),2.32-2.27(m,4H),2.14-2.00(m,45H), 1.88-1.73 (m, 5H).

[0047] (2) This step is the same as step (2)...

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Abstract

The invention provides a preparation method of 2-deoxy-D-glucose, comprising the steps of adding a catalyst, an iodide and water into compound (I), allowing full reaction, extracting a reacted liquid,concentrating, and recrystallizing to obtain compound (II), wherein R1 is one of formyl, acetyl, propionyl, benzoyl, benzyl, and t-butyldimethylsilyl and the catalyst is R2CH2SCH2X; subjecting the compound (II) to deprotection, and recrystallizing to obtain 2-deoxy-D-glucose. Glucal is used herein as a start material, and catalytic hydrolysis and deprotection are performed to obtain 2-deoxy-D-glucose; the preparation process has mild reaction conditions, a reaction reagent is easy to obtain, the reaction yield is high, an intermediate purifying method is simple and easy, catalyst usage is low, catalyst removal from the product is easy, the product has high purity, the reaction time is short, and reaction yield is high.

Description

technical field [0001] The invention belongs to the field of pharmaceutical production, in particular to a preparation method of 2-deoxy-D-glucose. Background technique [0002] Deoxysugar has important biological functions, and 2-deoxyribose, as an important backbone component of DNA, has important biological functions for the integrity and transmission of biological genetic information. In other respects, deoxysugars often appear in cardiac glycosides, antibiotics and anticancer drugs. Studies have found that in compounds with obvious biological activities, the sugar chain part regulates the kinetic properties of drugs, and plays an important role in drug transport, drug and action targets. plays an important role in the identification. Among them, 2-deoxy-D-glucose is not only a constituent fragment of many biologically active substances, but also has various biological activities, and is widely used in the fields of medicine, food and agriculture. 2-Deoxy-D-glucose has...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H3/08C07H1/00
CPCC07H1/00C07H3/08
Inventor 孙昊刘明倩刘鹏袁文蛟牛红军孙波
Owner TIANJIN MODERN VOCATIONAL TECH COLLEGE
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