Method for recycling byproduct associated during preparation process of mannose triflate intermediate 1,3,4,6-tetraacetyl-beta-D-mannose

A technology of trifluoromannose and tetraacetyl group, which is applied in the field of by-product conversion and utilization in the preparation process of intermediates, can solve the problems of low utilization rate and many associated by-products, etc., so as to improve yield, solve many reaction steps, and reduce environmental pollution. Effect

Inactive Publication Date: 2015-04-29
TIANJIN UNIV
View PDF3 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] The technical problem to be solved by the present invention is to provide a method for recycling the associated by-products in the preparation process of trifluoromannose intermediate 1,3,4,6-tetraacetyl-β-D-mannose, which overcomes the problems in the prior art. The defects of many by-products and low utilization rate in the preparation process of trifluoromannose intermediate 1,3,4,6-tetraacetyl-β-D-mannose

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
  • Method for recycling byproduct associated during preparation process of mannose triflate intermediate 1,3,4,6-tetraacetyl-beta-D-mannose
  • Method for recycling byproduct associated during preparation process of mannose triflate intermediate 1,3,4,6-tetraacetyl-beta-D-mannose

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] A method for recycling the by-products associated with trifluoromannose intermediate 1,3,4,6-tetraacetyl-β-D-mannose of the present invention comprises the following steps:

[0037] 174 grams of by-products associated with the multi-step one-pot method were added to 174 milliliters of acetic anhydride solution containing 0.17 grams of perchloric acid and 0.17 grams of tetrabutylammonium iodide, and the reaction temperature was controlled at 35°C while stirring. The addition was complete in 30 minutes, followed by stirring at room temperature for 1 hour. Cool down to -5°C, and add 174 ml of pre-cooled 30% hydrogen bromide glacial acetic acid solution to the mixture. After the addition was complete, the mixture was stirred at room temperature for 8 hours. Add 500 milliliters of dichloromethane to the reaction flask again, separate the layers to obtain the organic phase, wash with pre-cooled saturated brine and sodium bicarbonate solution, dry over anhydrous sodium sulfat...

Embodiment 2

[0039] The recycling method of the trifluoromannose intermediate 1,3,4,6-tetraacetyl-β-D-mannose associated by-products of the present invention comprises the following steps:

[0040] 174 grams of by-products associated with the step-by-step process were added to 522 milliliters of acetic anhydride solution containing 0.87 gram of perchloric acid and 0.87 gram of tetrabutylammonium iodide, stirred and controlled at 40° C. for the reaction temperature. The addition was complete in 1 hour, followed by another 2 hours of stirring at room temperature. The temperature was lowered to 0° C., and 522 ml of precooled 30% hydrogen bromide glacial acetic acid solution was added to the mixture. After the addition was complete, the mixture was stirred at room temperature for 12 hours. Add 500 milliliters of dichloromethane to the reaction flask again, separate the layers to obtain the organic phase, wash with pre-cooled saturated brine and sodium bicarbonate solution, dry over anhydrous ...

Embodiment 3

[0042] A method for recycling the by-products associated with trifluoromannose intermediate 1,3,4,6-tetraacetyl-β-D-mannose of the present invention comprises the following steps:

[0043]174 grams of by-products associated with the multi-step one-pot method were added to 348 milliliters of acetic anhydride solution containing 1.74 grams of perchloric acid and 1.74 grams of tetrabutylammonium iodide, and the reaction temperature was controlled at 38°C with stirring. The addition was complete in 45 minutes, followed by another hour of stirring at room temperature. Cool down to -2°C, and add 348 ml of pre-cooled 30% hydrogen bromide glacial acetic acid solution to the mixture. After the addition was complete, the mixture was stirred at room temperature for 10 hours. Add 500 milliliters of dichloromethane to the reaction flask again, separate the layers to obtain the organic phase, wash with pre-cooled saturated brine and sodium bicarbonate solution, dry over anhydrous sodium su...

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

PropertyMeasurementUnit
purityaaaaaaaaaa
purityaaaaaaaaaa
purityaaaaaaaaaa
Login to view more

Abstract

The invention relates to a method for recycling for recycling a byproduct associated during preparation process of mannose triflate intermediate 1,3,4,6-tetraacetyl-beta-D-mannose. The method comprises the following steps: adding the byproduct associated during preparation process of the mannose triflate intermediate 1,3,4,6-tetraacetyl-beta-D-mannose while stirring into a acetic anhydride mixed solution containing perchloric acid and tetrabutylammonium iodide to obtain a mixture, adding a pre-cooled hydrogen bromide glacial acetic acid solution into the mixture, stirring at room temperature, adding dichloromethane again into a reaction flask, separating to obtain an organic phase and washing to obtain a yellow bromide 2,3,4,6-tetraacetyl-alpha-D-mannose crude product; dissolving the crude product in a mixed solvent of acetic acid and acetic anhydride, cooling, adding a pre-cooled aqueous solution of sodium acetate, stirring and reacting; extracting with methylene chloride, washing, drying and filtering to remove the solvent to obtain a white solid 1,3,4,6-tetraacetyl-beta-D-mannose. The average yield of the recycled byproduct reaches 16%, the purity of the product is not less than 99.5%, the yield is increased and the environmental pollution is decreased.

Description

technical field [0001] The invention relates to a method for recycling associated by-products in the preparation process of trifluoromannose intermediate 1,3,4,6-tetraacetyl-β-D-mannose, belonging to the field of transformation and utilization of by-products in the intermediate preparation process . Background technique [0002] The full chemical name of trifluoromannose is 1,3,4,6-tetra-O-acetyl-2-O-trifluoromethanesulfonyl-β-D-mannose, which is a positron emission tomography (PET) imaging agent Synthetic precursor of 18F-FDG. As a tracer, 18F-FDG is widely used in basic experimental research and daily clinical diagnosis of cardiovascular and cerebrovascular, nerve and tumor, so there is a great demand for mannose trifluoride, among which mannose trifluoride intermediate is prepared with high quality and high efficiency 1 ,3,4,6-Tetra-O-acetyl-β-D-mannose is essential. [0003] In the prior art, there are two kinds of mannose as raw materials in the preparation method of...

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 Applications(China)
IPC IPC(8): C07H1/00C07H13/06C07H5/02
Inventor 马军安曾俊良聂晶
Owner TIANJIN UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap