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

Synthetic method of 3-deoxidized-D-sweet dew-2-octulosonic ammonium salt

A technology of ammonium octulose acid salt and synthesis method, which is applied in the direction of sugar compounds with non-glycosyl groups, chemical instruments and methods, compounds of Group 5/15 elements of the periodic table, etc., and can solve the problem that the total yield of the route is not high , environmental pollution, high cost, etc., to achieve the effect of simple operation, easy access to raw materials, and stable quality

Inactive Publication Date: 2013-04-03
SHAANXI NORMAL UNIV
View PDF3 Cites 3 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The reaction used in this method is relatively simple, but the dihydroxylation reaction requires the use of highly toxic osmium tetroxide, which will cause great pollution to the environment.
[0012] In summary, there are still problems such as low total yield, serious environmental pollution, and high cost in the synthesis technology of 3-deoxy-D-mannose-2-octanulose acid ammonium salt (KDO).

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
  • Synthetic method of 3-deoxidized-D-sweet dew-2-octulosonic ammonium salt
  • Synthetic method of 3-deoxidized-D-sweet dew-2-octulosonic ammonium salt
  • Synthetic method of 3-deoxidized-D-sweet dew-2-octulosonic ammonium salt

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Taking 10g of raw material D-mannose as an example, the method for synthesizing 3-deoxy-D-mannose-2-octulose acid ammonium salt consists of the following steps:

[0050] (1) Dissolve 10g of D-mannose in 42.7mL of N,N-dimethylformamide, add 27.3mL of 2,2-dimethoxypropane, stir well, add 1.43g of p-toluenesulfonic acid to the solution, Under the catalysis of p-toluenesulfonic acid, react at 25°C for 12 hours, the molar ratio of D-mannose to 2,2-dimethoxypropane, p-toluenesulfonic acid, N,N-dimethylformamide is 1: 4:0.15:10, stop stirring, and further purify, the specific process is: add 3g sodium bicarbonate to the reaction solution, quench the reaction, filter, the filtrate is depressurized by the oil pump to remove N,N-dimethylformamide, add 500mL Diluted with ethyl acetate, washed twice with water, washed once with saturated brine, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated and recrystallized with ethyl acetate to obtain 12.86 g...

Embodiment 2

[0066] Taking 10g of raw material D-mannose as an example, the method for synthesizing 3-deoxy-D-mannose-2-octulose acid ammonium salt consists of the following steps:

[0067] (1) Dissolve 10g of D-mannose in 65mL of N,N-dimethylformamide, add 23.9mL of 2,2-dimethoxypropane, stir well, add 0.95g of p-toluenesulfonic acid to the solution, Under the catalysis of p-toluenesulfonic acid, react at 25°C for 12 hours, the molar ratio of D-mannose to 2,2-dimethoxypropane, p-toluenesulfonic acid, N,N-dimethylformamide is 1: 3.5:0.1:15, stop stirring, and further purify, the specific process is: add 3g sodium bicarbonate to the reaction liquid, quench the reaction, filter, the filtrate is depressurized by the oil pump to remove N,N-dimethylformamide, add 500mL Diluted with ethyl acetate, washed twice with water, washed once with saturated brine, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated and recrystallized with ethyl acetate to obtain 12.1 g of ...

Embodiment 3

[0077] Taking 10g of raw material D-mannose as an example, the method for synthesizing 3-deoxy-D-mannose-2-octulose acid ammonium salt consists of the following steps:

[0078] (1) Dissolve 10g of D-mannose in 30mL of N,N-dimethylformamide, add 68mL of 2,2-dimethoxypropane, stir well, add 1.9g of p-toluenesulfonic acid to the solution, and Under the catalysis of p-toluenesulfonic acid, react at 25°C for 12 hours, the molar ratio of D-mannose to 2,2-dimethoxypropane, p-toluenesulfonic acid, N,N-dimethylformamide is 1:10 :0.2:7, stop stirring, and further purify, the specific process is: add 3g sodium bicarbonate to the reaction solution, quench the reaction, filter, the filtrate is decompressed through the oil pump to remove N,N-dimethylformamide, add 500mL acetic acid Diluted with ethyl ester, washed twice with water, washed once with saturated brine, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated and recrystallized with ethyl acetate to ob...

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 relates to a synthetic method of 3-deoxidized-D-sweet dew-2-octulosonic ammonium salt. The synthetic method comprises the following steps: using D-sweet dew as a raw material and performing the reaction on D-sweet dew and 2,2-dimethoxy propane; protecting hydroxy at 2 and 3 positions and 5 and 6 positions by isopropylidene to obtain an intermediate in a formula I; performing the reaction on a product in the formula I and 2-dimethoxy phosphoroso-2-dimethyl tertiary butyl silica ethyl acetate in a formula II to obtain an intermediate in a formula III; removing a silicyl oxide protecting group in a product in the formula III to form intramolecular hemiketal so as to obtain an intermediate in a formula IV; performing the deprotection, saponification and ammonium salt formation reaction on a product in the formula IV to obtain the final product 3-deoxidized-D-sweet dew-2-octulosonic ammonium salt. The method has the advantages of low price of the raw material, easiness for obtaining the raw material, mild reaction condition, simplicity and convenience for operation, high safety, high route total yield, simplicity for purification treatment on the final product and stable quality of the final product, and thus, the synthetic method disclosed by the invention enables the total cost to be greatly reduced and is suitable for the requirements on large-scale industrial production.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a synthesis method of 3-deoxy-D-mannose-2-octulose acid ammonium salt. Background technique [0002] 3-Deoxy-D-mannose-2-octanulose acid is one of the essential components of lipopolysaccharide in the cell wall of Gram-negative bacteria. Using 3-deoxy-D-mannose-2-octulose acid as the parent structure to modify the derivatives has a good inhibitory effect on Gram-negative bacteria; at the same time, 3-deoxy-D-mannose-2-octyl Ketoic acid can also be used as an antigen in some antibacterial (such as anti-meningitis) vaccines. The chemical structural formula of 3-deoxy-D-manno-2-octanulose acid is as follows: [0003] [0004] At present, the sources of 3-deoxy-D-manno-2-octanulose acid mainly include enzymatic synthesis and chemical synthesis. [0005] The enzyme synthesis method has the characteristics of mild reaction conditions, but due to the small sc...

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
IPC IPC(8): C07H7/033C07H1/00C07F9/40
CPCY02P20/55
Inventor 柴永海张琦徐芳园董洁冯颖乐
Owner SHAANXI NORMAL 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