Unlock instant, AI-driven research and patent intelligence for your innovation.

Preparation method of reagent for changing glucose hydroxyl configuration

A glucose and glucofuranose technology, applied in the preparation of sugar derivatives, chemical instruments and methods, sugar derivatives, etc., can solve the problems of wasting oxidants, difficult to separate products, and low purity of oxidation products

Inactive Publication Date: 2014-04-02
TIANJIN POLYTECHNIC UNIV
View PDF0 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In the above-mentioned chemical synthesis method to change the configuration reaction of the hydroxyl group on C in the sugar compound, either because the oxidation activity of the oxidant is weak, and the resulting oxidation product has low purity, many by-products, and the post-treatment is more complicated; in addition, the oxidant is excessive Larger, after the oxidation reaction, the oxidant is viscous and deposited on the bottom of the container, and a part of the oxidation product is coated in it, which not only wastes a lot of oxidant, but also the product is difficult to separate, and the viscous oxidant is difficult to filter , a large amount of solvent is needed to extract the product, and the amount of solvent consumed is large
Either because the purity of the obtained product is low, and column separation is required to obtain the pure product, which consumes a lot of solvent and time, resulting in low synthesis efficiency

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
  • Preparation method of reagent for changing glucose hydroxyl configuration

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] Embodiment 1: the preparation of oxidizing agent pyridinium dichromate (PDC)

[0015] Add 50ml of water and 50g of chromium trioxide into a 500ml four-necked bottle equipped with a thermometer and mechanical stirring, and add 40.3ml of pyridine dropwise to the reaction system while maintaining the temperature at 15-25°C. Then slowly add 200ml of acetone to the reaction liquid, filter the mixture after ice-cooling, and dry to obtain the oxidizing agent pyridinium dichromate (PDC).

Embodiment 2

[0016] Example 2: Oxidation of diisopropylidene-α-D-glucofuranose

[0017] Add 350ml of dry dichloromethane, 40.6g of pyridinium dichromate and 44.1g of acetic anhydride into a 1000ml four-neck flask equipped with a thermometer, condenser and mechanical stirring, and add di The solution of isopropylidene-α-D-glucofuranose (31.2g of diisopropylidene-α-D-glucofuranose+50ml of dry dichloromethane) was heated under reflux for 2h after the dropwise addition was completed. Then concentrate under reduced pressure (no more than 65°C), extract the concentrate with 200ml×2 ethyl acetate, filter the extract and residue through a column (100ml100-200 mesh silica gel, 10ml anhydrous magnesium sulfate liner on the head of the column), and use 600ml of ethyl acetate was used for elution, and the combined eluents were the oxidation products.

Embodiment 3

[0018] Example 3: Synthesis and Purification of Diisopropylidene-α-D-Allofuranose

[0019] The eluate in Example 2 was concentrated under reduced pressure (not exceeding 65° C.), and the concentrate was dissolved in ethanol solution (80 ml ethanol + 60 ml water). Maintain the temperature at 20-25°C under stirring, add sodium borohydride solution (5.6g sodium borohydride + 80ml water) dropwise to the solution within 0.5h, and react at room temperature for 3h. The reaction solution was extracted with 200ml×3 dichloromethane respectively, the organic layers were combined, washed with 100ml of water, and then dried with 100g of anhydrous magnesium sulfate overnight. Filtrate, concentrate the filtrate, and recrystallize the resulting solid with ether to obtain white crystals, which are the pure product of diisopropylidene-α-D-allofuranose.

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 preparation method of a reagent for changing glucose hydroxyl configuration. The preparation method is characterized in that water, chromium trioxide and pyridine react at a certain temperature, and are cooled, filtered and dried to obtain an oxidizing agent PDC (pyridinium dichromate); dichloromethane, the oxidizing agent PDC and acetic anhydride form a reaction system, a biisopropylidene-alpha-D-furan glucose solution is added into the system at the room temperature, the mixture is subjected to heating reflux and vacuum concentration, the concentrate is extracted with ethyl acetate, the extracting solution is filtered and eluted through a column, the eluents are combined, and vacuum concentration is conducted to obtain the oxide, a sodium borohydride solution is added into the oxide at certain temperature to react, the reaction liquid is extracted by dichloromethane after the reaction is finished, then anhydrous magnesium sulfate is used to dry the organic layer, the filtrate is filtered and concentrated, the obtained solid is recrystallized with diethyl ether, and then a pure product of biisopropylidene-alpha-D-furan allose is obtained.

Description

(1) Technical field: [0001] The invention relates to the field of organic synthesis pharmaceutical intermediates, in particular to a preparation method of a reagent for changing the configuration of glucose hydroxyl groups. (two) background technology: [0002] Oxidation-reduction reactions can be used to change the configuration of hydroxyl groups on carbon in carbohydrate compounds, but oxidation-reduction reactions are one of the difficulties in this type of synthetic reaction, mainly because it is quite difficult to implement oxidation reactions. If you need to select a certain activity The oxidant and the solvent used need to be dried, and the operation is more complicated. There are three main types of oxidants that people often oxidize monosaccharides with protective groups to ketose, namely dimethyl sulfoxide series, rubidium tetroxide series, and chromium trioxide series. Chromium trioxide series oxidants have received widespread attention because of their low pric...

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): C07H9/04C07H1/00
Inventor 祁世波
Owner TIANJIN POLYTECHNIC UNIV