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
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  • Abstract
  • Description
  • Claims
  • Application Information

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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

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  • 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

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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...

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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

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Application Information

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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
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