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2,3,4-Triacetyl-1-(nitro-2-pyridyl)mercapto-α-l-fucopyranoside

A technology of fucopyranoside and triacetyl, which is applied in the preparation of sugar derivatives, sugar derivatives, sugar derivatives, etc., can solve the problems of unstable intermediates, cumbersome synthetic routes, and small steric hindrance, and achieve Effects of changing stereoselectivity, simple synthesis methods, and cheap starting materials

Active Publication Date: 2019-04-16
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-(nitro-2-pyridyl)mercapto-α-l-fucopyranoside
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  • 2,3,4-Triacetyl-1-(nitro-2-pyridyl)mercapto-α-l-fucopyranoside

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

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

[0041] Weigh 0.486 g of FeCl3, 0.33 g of tetraacetylated fucose, and 0.155 g of 3-nitro-2-mercaptopyridine into parallel reaction tubes. Add 10 mL of dichloromethane and 0.5 mL of ionic liquid PFIL-1 [R1, R2, R3 = ethyl, n = 3, X = (CF3SO2)2N] under a nitrogen atmosphere, seal the reaction test tube, stir the reaction, and microwave irradiation using Intermittent, power 350W, irradiating for 5 minutes each time, stop irradiating 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, 0.21 g of Glycoside 1-1 was obtained with a yield of 49%. The ionic liquid can be reused without significant change in yield.

Embodiment 2

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

[0043] 0.33 g of tetraacetylated fucose and 0.155 g of 3-nitro-2-mercaptopyridine were placed in parallel reaction tubes. Under nitrogen atmosphere, add 10 mL of chloroform, 1 mL of ionic liquid PFIL-3 [R1, R2 = phenyl, n = 3, X = (CF3SO2)2N] and 0.345 mL of anhydrous SnCl4, seal the reaction tube, stir the reaction, microwave Irradiation is intermittent, with a power of 400W, irradiating for 5 minutes each time, and stopping the 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, 0.24 g of Glycoside 1-1 was obtained with a yield of 55%. The ionic liquid can be reused without significant change in yield.

Embodiment 3

[0044] Example 3: Preparation of 2,3,4-triacetyl-1-(3-nitro-2-pyridyl)mercapto-alpha-L-fucopyranoside

[0045] Weigh 0.591 g of Nd(OTf)3, 0.33 g of tetraacetylated fucose, and 0.155 g of 3-nitro-2-mercaptopyridine into parallel reaction tubes. Add 10 mL of 1,2-dichloroethane and 0.5 mL of ionic liquid PFIL-2 [R1, R2, R3 = phenyl, n = 4, X = (CF3SO2)2N] under a nitrogen atmosphere, seal the reaction tube, and stir the reaction. The microwave irradiation adopts intermittent type, the power is 500W, each irradiation is 5 minutes, and the irradiation is stopped 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, 0.25 g of Glycoside 1-1 was obtained with a yield of 59%. 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, in particular to 2,3,4-triacetyl-1-(nitro-2-pyridyl)-thiol-alpha-L-fucopyranoside and a synthesis method of a hydrolysis product thereof. The synthesis method includes using tetra-acetylated fucose and nitro-2-mercaptopyridine as starting materials, coordination functionalized ionic liquid containing phosphoryl groups as a reaction medium and Lewis acid as a catalyst, conducting glycosidation under microwave irradiation to obtain 2,3,4-triacetyl-1-(nitro-2-pyridyl)-thiol-alpha-L-fucopyranoside, and hydrolyzing the 2,3,4-triacetyl-1-(nitro-2-pyridyl)-thiol-alpha-L-fucopyranoside to obtain 1-(nitro-2-pyridyl)-thiol-alpha-L-fucopyranoside. The synthesis method has the advantages that the starting materials of the 1-(nitro-2-pyridyl)-thiol-alpha-L-fucopyranoside are cheap, synthesis approaches are simple and rapid, and the functionalized ionic liquid can be recycled, so that cost is reduced greatly.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to the synthesis of 2,3,4-triacetyl-1-(nitro-2-pyridyl)mercapto-alpha-L-fucopyranoside and hydrolyzed products. 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 v...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H17/02C07H1/00
CPCC07H1/00C07H17/02
Inventor 陆震宇梁洪泽梁炜达陈浩朱文明黄会燕陈伟婷陈梦莹李咏梅赵玲玲
Owner NINGBO UNIV
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