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2-deoxy-2-isorhodanate-1,3,4,6-tetra-O-benzyl-beta-D-glucopyranose, and synthetic method and application thereof

A technology of isothiocyanate and glucopyranose, applied in chemical instruments and methods, sugar derivatives, sugar derivatives, etc., can solve the problems of high risk and low yield, and achieve safe yield and side effects The effect of less product and easy operation

Active Publication Date: 2015-10-07
HUAIHAI INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This reaction requires the use of highly toxic thiophosgene, which is dangerous and has a low yield, which limits the application of this method to a certain extent.

Method used

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  • 2-deoxy-2-isorhodanate-1,3,4,6-tetra-O-benzyl-beta-D-glucopyranose, and synthetic method and application thereof
  • 2-deoxy-2-isorhodanate-1,3,4,6-tetra-O-benzyl-beta-D-glucopyranose, and synthetic method and application thereof
  • 2-deoxy-2-isorhodanate-1,3,4,6-tetra-O-benzyl-beta-D-glucopyranose, and synthetic method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Example 1, a 2-deoxy-2-isothiocyanate-1,3,4,6-tetra-O-benzyl- β -D-glucopyranose, its molecular formula is as follows:

[0022]

Embodiment 2

[0023] Example 2, a 2-deoxy-2-isothiocyanate-1,3,4,6-tetra-O-benzyl- β -D-glucopyranose synthetic method, it is characterized in that, first 2-deoxy-2-amino-1,3,4,6-tetra-O-benzyl- β -D-pyranose hydrochloride, carbon disulfide and triethylamine are reacted, and then reacted with p-toluenesulfonyl chloride to obtain 2-deoxy-2-isothiocyanate-1,3,4,6-tetra-O- Benzyl- β -D-glucopyranose; reaction with acetonitrile as solvent, 2-deoxy-2-amino-1,3,4,6-tetra-O-benzyl- β - The molar ratio of D-pyranose hydrochloride to carbon disulfide, triethylamine and p-toluenesulfonyl chloride is 1:1.2:3.0:1, the reaction temperature is 0°C, and the reaction time is 1 hour.

Embodiment 3

[0024] Example 3, a 2-deoxy-2-isothiocyanate-1,3,4,6-tetra-O-benzyl- β -D-glucopyranose synthetic method, it is characterized in that, first 2-deoxy-2-amino-1,3,4,6-tetra-O-benzyl- β -D-pyranose hydrochloride, carbon disulfide and triethylamine are reacted, and then reacted with p-toluenesulfonyl chloride to obtain 2-deoxy-2-isothiocyanate-1,3,4,6-tetra-O- Benzyl- β -D-glucopyranose; reaction with acetonitrile as solvent, 2-deoxy-2-amino-1,3,4,6-tetra-O-benzyl- β - The molar ratio of D-pyranose hydrochloride to carbon disulfide, triethylamine and p-toluenesulfonyl chloride is 1.2:1:3.5:1.2, the reaction temperature is 0°C, and the reaction time is 2 hours.

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Abstract

The invention relates to 2-deoxy-2-isorhodanate-1,3,4,6-tetra-O-benzyl-beta-D-glucopyranose. The invention also relates to a synthetic method for 2-deoxy-2-isorhodanate-1,3,4,6-tetra-O-benzyl-beta-D-glucopyranose. The synthetic method comprises the following concrete steps: reacting 2-deoxy-2-amino-1,3,4,6-tetra-O-benzyl-beta-D-pyranose hydrochloride and carbon disulfide with triethylamine; and then reacting a reaction product with p-toluene sulfonyl chloride so as to obtain 2-deoxy-2-isorhodanate-1,3,4,6-tetra-O-benzyl-beta-D-glucopyranose, wherein acetonitrile is used as a solvent for the reaction, reaction temperature is 0 DEG C, and reaction time is 1 to 2 h. The synthetic method has the advantages of easy and safe operation, small environmental pollution, high yield and simple post-treatment. The prepared 2-deoxy-2-isorhodanate-1,3,4,6-tetra-O-benzyl-beta-D-glucopyranose can be used as an organic synthesis intermediate for synthesis of a glucosamine derivative.

Description

technical field [0001] The present invention relates to the field of organic synthesis, and relates to an isothiocyanate, in particular to a 2-deoxy-2-isothiocyanate-1,3,4,6-tetra-O-benzyl-β- D-glucopyranose, the present invention also relates to the synthesis method of the compound, and the present invention also relates to the use of the compound. Background technique [0002] Isothiocyanate is an important class of organic synthesis intermediates, which can participate in a variety of organic reactions, and is used to synthesize various types of compounds containing sulfur, nitrogen, and oxygen, especially heterocyclic compounds. The heterocyclic compounds synthesized are large Most of them have biological activity, such as antibacterial, insecticide, herbicide, etc. in pesticides, antibacterial, anti-inflammatory, and treatment of cancer and other diseases in medicine. [0003] As a natural monosaccharide, D-glucosamine is mainly obtained from the hydrolysis of chitin. ...

Claims

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Application Information

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IPC IPC(8): C07H15/18C07H1/00
Inventor 刘玮炜程峰昌殷龙李曲祥
Owner HUAIHAI INST OF TECH
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