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2,3,4-triacetyl-1-(5-trifluoromethyl-2-pyridyl) mercapto-alpha-L-fucopyranoside

A technology of fucopyranoside and trifluoromethyl is applied in the preparation of sugar derivatives, sugar derivatives, sugar derivatives, etc., and can solve the problems of unstable intermediates, small steric hindrance, and complicated synthesis routes. To achieve the effect of changing stereoselectivity, cheap starting materials, and simple synthesis methods

Active Publication Date: 2017-02-15
NINGBO UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Traditional glycoside synthesis methods (such as Chinese patents 95118925.5, 201010101523.7, etc.) have the following problems: poor repeatability, poor stereoselectivity, cumbersome synthetic routes, expensive raw materials or unstable intermediates, etc. It is difficult to meet the requirements of purity and large-scale markets , so it is necessary to research and develop new synthetic methods
Due to the small steric hindrance of Lewis acid metal salts, it is difficult to fully control the stereoselectivity of glycosylation during the catalytic glycosylation process
Therefore, in traditional catalytic systems, stereoselectivity is not ideal in most cases

Method used

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  • 2,3,4-triacetyl-1-(5-trifluoromethyl-2-pyridyl) mercapto-alpha-L-fucopyranoside

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Example 1: Preparation of 2,3,4-triacetyl-1-(5-trifluoromethyl-2-pyridyl)mercapto-alpha-L-fucopyranoside

[0039] Weigh 0.486 g of FeCl 3 , 0.33 g of tetraacetylated fucose, and 0.179 g of 5-trifluoromethyl-2-mercaptopyridine were placed in parallel reaction tubes. Add 10mL dichloromethane and ionic liquid PFIL-1[R 1 , R 2 , R 3 =ethyl, n=3, X=(CF 3 SO 2 ) 2 N] 0.5mL, airtight reaction test tube, stirring reaction, microwave irradiation using intermittent, power 350W, each irradiation 5 minutes, stop irradiation for 1 minute. Reaction was carried out for 5 hours, and the temperature was controlled at about 40 degrees Celsius. After the reaction was completed, water was added to terminate the reaction. After separation by silica gel column, 0.29 g of Glycoside 1 was obtained with a yield of 65%. The ionic liquid can be reused without significant change in yield.

Embodiment 2

[0040] Example 2: Preparation of 2,3,4-triacetyl-1-(5-trifluoromethyl-2-pyridyl)mercapto-alpha-L-fucopyranoside

[0041] 0.33 g of tetraacetylated fucose and 0.179 g of 5-trifluoromethyl-2-mercaptopyridine were placed in parallel reaction tubes. Add 10mL trichloromethane and ionic liquid PFIL-3[R 1 , R 2 =phenyl, n=3, X=(CF 3 SO 2 ) 2 N] 1mL and 0.345mL of anhydrous SnCl 4 , airtight reaction test tube, stirring reaction, microwave irradiation using intermittent, power 400W, each irradiation 5 minutes, stop irradiation for 1 minute. Reaction was carried out for 3 hours, and the temperature was controlled at about 60 degrees Celsius. After the reaction was completed, water was added to terminate the reaction. After separation by silica gel column, 0.33 g of Glycoside 1 was obtained with a yield of 73%. The ionic liquid can be reused without significant change in yield.

Embodiment 3

[0042] Example 3: Preparation of 2,3,4-triacetyl-1-(5-trifluoromethyl-2-pyridyl)mercapto-alpha-L-fucopyranoside

[0043] Weigh 0.591 g of Nd(OTf) respectively 3 , 0.33 g of tetraacetylated fucose, and 0.179 g of 5-trifluoromethyl-2-mercaptopyridine were placed in parallel reaction tubes. Add 10mL of 1,2-dichloroethane and ionic liquid PFIL-2[R 1 , R 2 , R 3 =phenyl, n=4, X=(CF 3 SO 2 ) 2 N] 0.5mL, airtight reaction test tube, stirring reaction, microwave irradiation using intermittent, power 500W, each irradiation 5 minutes, stop irradiation for 1 minute. Reaction was carried out for 5 hours, and the temperature was controlled at about 80 degrees Celsius. After the reaction was completed, water was added to terminate the reaction. After separation by silica gel chromatography, 0.31 g of Glycoside 1 was obtained with a yield of 70%. The ionic liquid can be reused without significant change in yield.

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Abstract

The invention relates to the field of chemical synthesis and particularly discloses synthesis of 2,3,4-triacetyl-1-(5-trifluoromethyl-2-pyridyl) mercapto-alpha-L-fucopyranoside and hydrolysate. Tetraacetylated fucose and 5-trifluoromethyl-2-mercaptopyridine are taken as starting materials, a PFIL (phosphoryl coordination functionalized ionic liquid)-containing mixed solvent is taken as a reaction medium, the Lewis acid is taken as a catalyst, 2,3,4-triacetyl-1-(5-trifluoromethyl-2-pyridyl) mercapto-alpha-L-fucopyranoside is prepared through glycosylation under microwave irradiation, and then 1-(5-trifluoromethyl-2-pyridyl) mercapto-alpha-L-fucopyranoside is obtained through hydrolysis. The starting materials for preparing 1-(5-trifluoromethyl-2-pyridyl) mercapto-alpha-L-fucopyranoside are relatively cheap, the synthesis means is simple and rapid, the functionalized ionic liquid can be reused, and the cost is reduced greatly.

Description

technical field [0001] The present invention relates to the technical field of chemical synthesis, in particular to 2,3,4-triacetyl-1-(5-trifluoromethyl-2-pyridyl)mercapto-alpha-L-fucopyranoside and its hydrolyzate synthesis. Background technique [0002] Carbohydrates, proteins and nucleic acids make up important living substances. With the development of modern science and technology, the research on sugar compounds has also made great progress. Related researches are further divided into subfields such as glycochemistry, glycopharmaceuticals, glycobiology, glycoengineering, and glycoomics. Sugar is not only an energy substance, but more importantly, it is closely related to the life process. Sugar can be used as a biological information molecule to participate in many processes such as immune regulation, cell differentiation, and embryonic development. Pyridine groups and sulfur-containing compounds have biological activity, and have pyridine structures and sulfur ele...

Claims

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Application Information

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IPC IPC(8): C07H17/02C07H1/00C12Q1/34
CPCC07H1/00C07H17/02C12Q1/34Y02P20/54
Inventor 陈浩
Owner NINGBO UNIV
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