Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

2,3,4-Triacetyl-1-(6methyl-5nitro-2pyridyl)mercapto-α-l-fucopyranoside

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, small steric hindrance, and complicated synthetic routes, and achieves The effect of changing stereoselectivity, cheap starting materials, and simple synthetic means

Active Publication Date: 2019-04-16
NINGBO UNIV
View PDF7 Cites 0 Cited by
  • 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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • 2,3,4-Triacetyl-1-(6methyl-5nitro-2pyridyl)mercapto-α-l-fucopyranoside
  • 2,3,4-Triacetyl-1-(6methyl-5nitro-2pyridyl)mercapto-α-l-fucopyranoside
  • 2,3,4-Triacetyl-1-(6methyl-5nitro-2pyridyl)mercapto-α-l-fucopyranoside

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Example 1: Preparation of 2,3,4-triacetyl-1-(6-methyl-5-nitro-2-pyridyl)mercapto-alpha-L-fucopyranoside

[0039] Weigh 0.486 g of FeCl3, 0.33 g of tetraacetylated fucose, and 0.17 g of 6-methyl-5-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 chromatography, 0.23 g of Glycoside 1 was obtained with a yield of 52%. The ionic liquid can be reused without significant change in yield.

Embodiment 2

[0040] Example 2: Preparation of 2,3,4-triacetyl-1-(6-methyl-5-nitro-2-pyridyl)mercapto-alpha-L-fucopyranoside

[0041] 0.33 g of tetraacetylated fucose and 0.17 g of 6-methyl-5-nitro-2-mercaptopyridine were placed in parallel reaction tubes. Under a 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. React for 3 hours, and the temperature is controlled at about 60 degrees Celsius. After the reaction was completed, water was added to terminate the reaction. After separation by silica gel chromatography, 0.256 g of Glycoside 1 was obtained with a yield of 58%. The ionic liquid can be reused without significant change in yield.

Embodiment 3

[0042] Example 3: Preparation of 2,3,4-triacetyl-1-(6-methyl-5-nitro-2-pyridyl)mercapto-alpha-L-fucopyranoside

[0043] Weigh 0.591 g of Nd(OTf)3, 0.33 g of tetraacetylated fucose, and 0.17 g of 6-methyl-5-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, 0.314 g of Glycoside 1 was obtained with a yield of 71%. The ionic liquid can be reused without significant change in yield.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention belongs to the field of chemical synthesis, and more specifically discloses a synthesis method of 2,3,4-triacetyl-1-(6-methyl-5-nitro-2-pyridyl) mercapto-alpha-L-fucose pyranoside and a hydrolysate. According to the synthesis method, tetra-acetylated-fucose and 6-methyl-5-nitro-2-mercaptopyridine is taken as a starting raw material, a coordination functionalized ionic liquid containing phosphoryl groups is taken as a reaction medium, Lewis acid is taken as a catalyst, glycosylation is carried out under microwave irradiation so as to prepare 2,3,4-triacetyl-1-(6-methyl-5-nitro-2-pyridyl) mercapto-alpha-L-fucose pyranoside, and then hydrolysis is carried out so as to obtain 1-(6-methyl-5-nitro-2-pyridyl) mercapto-alpha-L-fucose pyranoside. The starting material of 1-(6-methyl-5-nitro-2-pyridyl) mercapto-alpha-L-fucose pyranoside is relatively cheap; the synthesis method is simple and rapid; the functionalized ionic liquid can be recycled; and 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-(6-methyl-5-nitro-2-pyridyl)mercapto-alpha-L-fucopyranoside, Its hydrolyzate and its preparation method. 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 a...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(China)
IPC IPC(8): C07H17/02C07H1/00
CPCC07H1/00C07H17/02
Inventor 陈伟婷梁洪泽梁炜达陈浩朱文明黄会燕陆震宇陈梦莹李咏梅赵玲玲
Owner NINGBO UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com