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Preparation method of 2-C-methyl-D-ribotide-1,4-lactone

A ribonic acid and methyl technology, applied in the preparation of 2-C-methyl-D-ribonic acid-1,4-lactone, the field of lactone compounds, can solve the problems of low yield, high cost and high risk factor , to achieve the effect of reasonable process, low cost and simple operation

Inactive Publication Date: 2015-06-10
SHANGHAI INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] Aiming at the above-mentioned technical problems in the prior art, the present invention provides a kind of 2-C-methyl-D-ribonic acid-1,4-lactone Preparation method, the preparation method of the described 2-C-methyl-D-ribonic acid-1,4-lactone solves the problem of preparing 2-C-methyl-D-ribonic acid-1 in the prior art , the technical problems of low yield, high cost and high risk coefficient of the 4-lactone method

Method used

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  • Preparation method of 2-C-methyl-D-ribotide-1,4-lactone
  • Preparation method of 2-C-methyl-D-ribotide-1,4-lactone

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Embodiment 1

[0034] (1) The first step reaction feeds such as The table below Show:

[0035] raw material name Specification MW (g / mol) Feeding amount mol% (eq) D-glucose 99％ 180.16 352g 2.0 Dimethylamine CP. 45 45 / 250ml 1.02 glacial acetic acid CP. 60 56ml 1.0 ethanol CP. -- 250ml 1.5(v / m)

[0036] At 25°C, add D-glucose, glacial acetic acid and ethanol into a 1L four-neck flask with magnetic stirring and a thermometer, stir to form a suspension, cool to -5-0°C in an ice-salt bath, then add dimethylamine dropwise Ethanol solution (the molar ratio of D-grape and dimethylamine is nearly 2:1), keep the temperature below 17°C, keep it constant for 15 minutes, then raise the temperature to 75°C within 30 minutes, react for 30 minutes, then cool down to 55°C within 30 minutes, and continue the reaction for 2 hours , use thin-layer chromatography to track until the raw materials are completely converted, stop heating, cool down to 2...

Embodiment 2

[0043] (1) The first step reaction feeds such as The table below Show:

[0044] raw material name Specification MW (g / mol) Feeding amount mol% (eq) D-glucose 99％ 180.16 176g 1.0 Dimethylamine CP. 45 45 / 250ml 1.02 glacial acetic acid CP. 60 56ml 1.0 ethanol CP. -- 250ml 1.5(v / m)

[0045]At 25°C, add D-glucose, glacial acetic acid and ethanol into a 1L four-neck flask with magnetic stirring and a thermometer, stir to form a suspension, cool to -5-0°C in an ice-salt bath, then add dimethylamine dropwise Ethanol solution (the molar ratio of D-grape and dimethylamine is nearly 1:1), the reaction is exothermic, keep the temperature below 17°C, keep it constant for 15 minutes, then raise the temperature to 75°C within 30 minutes, react for 30 minutes, then cool down to 55°C within 30 minutes , continue the reaction for 2 h, use thin layer chromatography to track until the raw materials are completely converted, stop heat...

Embodiment 3

[0051] (1) The first step reaction feeds such as The table below Show:

[0052] raw material name Specification MW (g / mol) Feeding amount mol% (eq) D-glucose 99％ 180.16 176g 1.0 Dimethylamine CP. 45 90 / 250ml 2.04 glacial acetic acid CP. 60 56ml 1.0 ethanol CP. -- 250ml 1.5(v / m)

[0053] At 25°C, add D-glucose, glacial acetic acid and ethanol into a 1L four-neck flask with magnetic stirring and a thermometer, stir to form a suspension, cool to -5-0°C in an ice-salt bath, then add dimethylamine dropwise Ethanol solution (the molar ratio of D-grape and dimethylamine is nearly 1:2), the reaction is exothermic, keep the temperature below 17°C, keep it constant for 15 minutes, then raise the temperature to 75°C within 30 minutes, react for 30 minutes, then cool down to 55°C within 30 minutes , continue the reaction for 2 h, use thin layer chromatography to track until the raw materials are completely converted, stop hea...

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Abstract

The invention provides a preparation method of 2-C-methyl-D-ribotide-1,4-lactone, which comprises the steps of synthesizing 1-deoxy-1-(N,N amino)-D-fructose by taking D-glucose as a raw material, and carrying out rearrangement reaction through the 1-deoxy-1-(N,N amino)-D-fructose so as to obtain 2-C-methyl-D-ribotide-1,4-lactone. The method disclosed by the invention is rational in process, simple in operation, and low in cost, the yield is increased to a certain extent, and the industrialization can be realized well.

Description

technical field [0001] The invention belongs to the field of chemical industry, and in particular relates to a lactone compound, in particular to a preparation method of 2-C-methyl-D-ribonic acid-1,4-lactone. Background technique [0002] 2-C-methyl-D-ribonic acid-1,4-lactone is an important pharmaceutical intermediate, which can be used to prepare nucleoside drugs. Nucleoside drugs have a wide range of application fields in antiviral and antitumor aspects, such as anti-hepatitis C virus (abbreviated as HCV) drugs. [0003] 2-C-Methyl-D-ribono-1,4-lactone [0004] Molecular formula: C6H10O5, molecular weight: 162.14, structural formula as follows: [0005] [0006] Currently known preparation methods for the above-mentioned structural lactones: D-fructose (R.L.Wistler, "Methods Carbohud Chem.", 1963, 2, 484-485") can be used as a raw material, and the yield is about 10%. This route uses highly toxic reagents Sodium cyanide is very dangerous, and the obtained product is...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/33
CPCC07D307/33
Inventor 余焓廉祥何慧红高静韩生
Owner SHANGHAI INST OF TECH