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2, 3, 4-triacetyl-1-(5-bromo-2-pyridyl) sulfydryl-ahpha-L-fucose pyranoside

A fucopyranoside and triacetyl technology, which is applied in the preparation of sugar derivatives, sugar derivatives, and sugar derivatives, can solve the problems of unstable intermediates, cumbersome synthetic routes, and small steric hindrance, and achieves The effect of changing stereoselectivity, simple synthesis method, and cheap starting materials

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-bromo-2-pyridyl) sulfydryl-ahpha-L-fucose pyranoside
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  • 2, 3, 4-triacetyl-1-(5-bromo-2-pyridyl) sulfydryl-ahpha-L-fucose pyranoside

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

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

[0039] Weigh 0.486 g of FeCl 3 , 0.33 g of tetraacetylated fucose, and 0.19 g of 5-bromo-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 chromatography, 0.25 g of Glycoside 1 was obtained with a yield of 50%. Mass spectrum (positive ion mode): m / z 462.02 (M+H) + . The ionic liquid can be reused without significant change in yield.

Embodiment 2

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

[0041] 0.33 g of tetraacetylated fucose and 0.19 g of 5-bromo-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, 0.258 g of Glycoside 1 was obtained with a yield of 56%. The ionic liquid can be reused without significant change in yield.

Embodiment 3

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

[0043] Weigh 0.591 g of Nd(OTf) respectively 3 , 0.33 g of tetraacetylated fucose, and 0.19 g of 5-bromo-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 column, 0.336 g of Glycoside 1 was obtained with a yield of 73%. 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 2, 3, 4-triacetyl-1-(5-bromo-2-pyridyl) sulfydryl-ahpha-L-fucose pyranoside. Four-acetylated fucose and 5-bromine-2-mercapto pyridine are adopted as initial raw materials and a phosphoryl ligand functionalized ionic liquid is adopted as a reaction medium. Meanwhile, lewis acid is adopted as a catalyst. Under the effect of microwave irradiation, the glycosylation reaction is conducted to prepare the 2, 3, 4-triacetyl-1-(5-bromo-2-pyridyl) sulfydryl-ahpha-L-fucose pyranoside. After that, the hydrolysis reaction is conducted to obtain the 1-(5-bromo-2-pyridyl) sulfydryl-ahpha-L-fucose pyranoside. The initial raw materials of the prepared 1-(5-bromo-2-pyridyl) sulfydryl-ahpha-L-fucose pyranoside are relatively cheap, and the synthesis means of the 1-(5-bromo-2-pyridyl) sulfydryl-ahpha-L-fucose pyranoside is simple and fast. Moreover, the functionalized ionic liquid can be repeatedly used, so that the cost is greatly reduced.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to 2,3,4-triacetyl-1-(5-bromo-2-pyridyl)mercapto-α-L-fucopyranoside. 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 elements in various drugs and pesticides. Designing, sy...

Claims

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Application Information

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IPC IPC(8): C07H17/02C07H1/00C12Q1/34
CPCC07H1/00C07H17/02C12Q1/34
Inventor 陈伟婷
Owner NINGBO UNIV
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