Method for purifying 1,3,4,6-tetra-O-acetyl-2-O-triflat-beta-D-mannopyranose intermediate

A technology of trifluoromannose and purification method, applied in the field of purification of trifluoromannose intermediate, 1,3,4,6-tetraacetyl-β-D-mannose, can solve the problem of yield and purity. High, affecting the yield and purity of trifluoromannose, to achieve the effect of good stability and long shelf life

Active Publication Date: 2014-04-23
无锡市江原实业技贸有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] For this reason, the technical problem to be solved by the present invention is that the yield and the purity of the trifluoromannose intermediate 1,3,4,6-tetraacetyl-β-D-mannose synthesized in the prior art are not high and thus affect The problem of the yield and purity of the synthesized trifluoromannose, and then provide a purification method that can significantly improve the yield and purity of 1,3,4,6-tetraacetyl-β-D-mannose

Method used

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  • Method for purifying 1,3,4,6-tetra-O-acetyl-2-O-triflat-beta-D-mannopyranose intermediate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] The purification method of trifluoromannose intermediate 1,3,4,6-tetraacetyl-β-D-mannose described in this example comprises the following steps:

[0032] Add 50mL of the mixed liquid containing n-butanol and ethylene glycol monomethyl ether in a three-necked flask, the ratio of the volume of n-butanol and ethylene glycol monomethyl ether is 6:1, add the above-mentioned 1,3, 4,6-tetraacetyl-β-D-mannose crude product 10g, and the solution was heated to 80 ° C until the 1,3,4,6-tetraacetyl-β-D-mannose crude product was completely dissolved, then The temperature of the above solution was lowered to 8°C, and allowed to stand for crystallization for 1 hour, and the solution of the above crystallization was filtered, and 3 mL of n-butanol solution was added to wash the above filtered crystals, and the washing was repeated for 2-3 times, and the washed crystals were placed in vacuum at 45°C. After drying for 8 hours, 1,3,4,6-tetraacetyl-β-D-mannose crystals were obtained.

Embodiment 2

[0034] The purification method of trifluoromannose intermediate 1,3,4,6-tetraacetyl-β-D-mannose described in this example comprises the following steps:

[0035] Add 100mL of the mixed liquid containing n-butanol and ethylene glycol monomethyl ether in a three-necked flask, the ratio of the volume of n-butanol and ethylene glycol monomethyl ether is 6:1, add the above-mentioned 1,3, 10 g of crude 4,6-tetraacetyl-β-D-mannose, and heating the solution to 100° C. until the crude 1,3,4,6-tetraacetyl-β-D-mannose is completely dissolved, Subsequently, the above-mentioned dissolving solution was cooled to 10° C., and allowed to stand for crystallization for 2 hours. The above-mentioned crystallization solution was filtered, and 5 mL of n-butanol solution was added to wash the above-mentioned filtered crystals, and the washing was repeated for 2-3 times. °C for 10 hours under vacuum to obtain the 1,3,4,6-tetraacetyl-β-D-mannose crystals.

Embodiment 3

[0037] The purification method of trifluoromannose intermediate 1,3,4,6-tetraacetyl-β-D-mannose described in this example comprises the following steps:

[0038] Add 150mL of the mixed liquid containing n-butanol and ethylene glycol monomethyl ether in a three-necked flask, the volume ratio of n-butanol and ethylene glycol monomethyl ether is 6:1, add the above prepared 1,3, 10 g of crude 4,6-tetraacetyl-β-D-mannose, and heating the solution to 110° C. until the crude 1,3,4,6-tetraacetyl-β-D-mannose is completely dissolved, Subsequently, the above-mentioned solution was cooled to 15° C., and allowed to stand for crystallization for 3 hours, the solution of the above-mentioned crystal was filtered, and 7 mL of n-butanol solution was added to wash the above-mentioned filtered crystal, and the washing was repeated for 2-3 times, and the washed crystal was placed at 55 °C for 12 hours under vacuum to obtain the 1,3,4,6-tetraacetyl-β-D-mannose crystals.

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Abstract

The invention provides a method for purifying a 1,3,4,6-tetra-O-acetyl-2-O-triflat-beta-D-mannopyranose intermediate. The method comprises the following steps: adding a crude 1,3,4,6-tetraacetyl-beta-D-mannopyranose product into mixed liquid containing n-butyl alcohol and 2-methoxyethanol; heating the crude 1,3,4,6-tetraacetyl-beta-D-mannopyranose product until the crude 1,3,4,6-tetraacetyl-beta-D-mannopyranose product is dissolved; cooling the crude 1,3,4,6-tetraacetyl-beta-D-mannopyranose product until the crude 1,3,4,6-tetraacetyl-beta-D-mannopyranose product is completely crystallized; performing filtering, washing and drying to obtain the 1,3,4,6-tetra-O-acetyl-2-O-triflat-beta-D-mannopyranose intermediate, namely a 1,3,4,6-tetraacetyl-beta-D-mannopyranose crystal. The yield and purity of the 1,3,4,6-tetraacetyl-beta-D-mannopyranose are remarkably improved, so that the problems of low yield and low purity of the synthesized 1,3,4,6-tetra-O-acetyl-2-O-triflat-beta-D-mannopyranose intermediate namely 1,3,4,6-tetraacetyl-beta-D-mannopyranose in the prior art are solved.

Description

technical field [0001] The invention belongs to the field of separation and purification, and in particular relates to a method for purifying a trifluoromannose intermediate, that is, 1,3,4,6-tetraacetyl-β-D-mannose. Background technique [0002] Trifluoromannose, whose chemical name is 1,3,4,6-tetra-O-acetyl-2-O-trifluoromethanesulfonyl-β-D-mannose, is a synthetic PET imaging agent 18 Precursor of F-FDG. Currently, 18 F-FDG is the most widely used tracer in positron emission tomography (PET) imaging. It is not only widely used in laboratory research, but also widely used in daily clinical diagnosis of cardiovascular, neurological and tumor. Accounting for more than 90% of the clinical application of PET imaging, thus increasing the demand for mannose trifluoride, thus requiring higher requirements for the yield and purity of mannose trifluoride synthesized in the prior art to meet the three Huge demand for mannose. [0003] At present, the industrial production of trifl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H13/06C07H1/06
Inventor 邹霈吴昊刘娅灵谢敏浩王洪勇吴军
Owner 无锡市江原实业技贸有限公司
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