Preparation method of 2, 3, 4, 6-tetra-O-acetyl-glucopyranose

A technology of glucopyranose and acetyl, which is applied in the preparation of sugar derivatives, chemical instruments and methods, sugar derivatives, etc., can solve problems such as environmental hazards, increase production costs, and increase processing difficulty, so as to reduce processing difficulty, The effect of less usage and reduction of production cost

Pending Publication Date: 2022-07-22
江西艾立斯特生物科技有限公司
View PDF2 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Because tetrahydrofuran is expensive, harmful to the environment, and it is soluble in water, the waste water that adopts this method to prepare 2,3,4,6-tetra-O-acetyl-glucopyranose contains a large amount of tetrahydrofuran, after increasing waste water Processing difficulty, increase production cost

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 2, 3, 4, 6-tetra-O-acetyl-glucopyranose

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Put 40g of a mixed solution of dichloromethane and tetrahydrofuran (v:v=1:2) into a 250mL flask, add 1,2,3,4,6-penta-O-acetyl-glucopyranose (10g , 25.64 mmol) until all dissolved and benzylamine (3.08 mL, 28.20 mmol) was added. Stir at room temperature and react for 6h. TLC detected the end of the reaction (8% H 2 SO 4 -EtOH solution for carbonization), Rf: 0.7 (cyclohexane:ethyl acetate=1.5:1). 84.6 mL of 1 mol / L hydrochloric acid was added to the reaction system, stirred for 2 h, the layers were separated, the aqueous phase was extracted and washed with 40 mL of dichloromethane (twice), the organic phase was collected, and evaporated to dryness to obtain 2,3,4,6-tetra-O -Acetyl-glucopyranose. The yield was 99.4%.

[0027] After the tetrahydrofuran in the waste water is recovered, anhydrous sodium sulfate of 1 / 5 the weight of hydrofuran is added to remove water, which can be continued to be used as a reaction solvent.

Embodiment 2

[0029] Put 40g of a mixed solution of dichloromethane and tetrahydrofuran (v:v=1:2) into a 250mL flask, add 1,2,3,4,6-penta-O-acetyl-glucopyranose (10g , 25.64 mmol) until all dissolved and benzylamine (3.08 mL, 28.20 mmol) was added. Stir at room temperature and react for 6h. TLC detected the end of the reaction (8% H 2 SO 4 -EtOH solution for carbonization), Rf: 0.7 (cyclohexane:ethyl acetate=1.5:1). 112.8mL of 1mol / L hydrochloric acid was added to the reaction system, stirred for 2h, the layers were separated, the aqueous phase was extracted and washed with 40mL of dichloromethane (twice), the organic phase was collected, and evaporated to dryness to obtain 2,3,4,6-tetra-O -Acetyl-glucopyranose. The yield was 99.1%.

[0030] After the tetrahydrofuran in the waste water is recovered, anhydrous sodium sulfate of 1 / 5 of the weight of tetrahydrofuran is added to remove water, which can continue to be used as a reaction solvent.

Embodiment 3

[0032]Put 40g of a mixed solution of dichloromethane and tetrahydrofuran (v:v=1:1) into a 250mL flask, add 1,2,3,4,6-penta-O-acetyl-glucopyranose (10g , 25.64 mmol) until all dissolved and benzylamine (3.08 mL, 28.20 mmol) was added. Stir at room temperature and react for 6h. TLC detected the end of the reaction (8% H 2 SO 4 -EtOH solution for carbonization), Rf: 0.7 (cyclohexane:ethyl acetate=1.5:1). 84.6 mL of 1 mol / L hydrochloric acid was added to the reaction system, stirred for 2 h, the layers were separated, the aqueous phase was extracted and washed with 40 mL of dichloromethane (twice), the organic phase was collected, and evaporated to dryness to obtain 2,3,4,6-tetra-O -Acetyl-glucopyranose. The yield was 98.8%.

[0033] After the tetrahydrofuran in the waste water is recovered, anhydrous sodium sulfate of 1 / 5 of the weight of tetrahydrofuran is added to remove water, which can continue to be used as a reaction solvent.

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 2, 3, 4, 6-tetra-O-acetyl-glucopyranose, and belongs to the technical field of organic synthesis. According to the 1, 2, 3, 4, 6-5-O-acetyl-glucopyranose disclosed by the invention, a mixed solution of dichloromethane and tetrahydrofuran is used as a reaction solvent, and terminal acetyl is removed under the action of benzylamine. And after the reaction is finished, adding 1mol / L hydrochloric acid into the reaction system, stirring for 2 hours, extracting and washing with dichloromethane, collecting an organic phase, and drying by distillation to obtain the 2, 3, 4, 6-tetra-O-acetyl-glucopyranose. As a tetrahydrofuran reagent is relatively expensive and has great pollution to the environment, the preparation method has the advantages that the use amount of tetrahydrofuran is small, the production cost is reduced, only a small amount of tetrahydrofuran is contained in wastewater, the tetrahydrofuran in the wastewater can be recycled after being recycled, the wastewater post-treatment difficulty is reduced, and the method is suitable for industrial production.

Description

technical field [0001] The invention relates to a preparation method of 2,3,4,6-tetra-O-acetyl-glucopyranose, and belongs to the technical field of organic synthesis. Background technique [0002] In recent years, sugar research has become another emerging frontier and hotspot in chemistry and life sciences. With the in-depth research on the structure and function of sugar, people realize that sugar is not only the support and energy storage unit of the organism, but also an important biological information substance in the organism, participating in many physiological processes, and its many biological functions gradually Known to be revealed. Glycochemistry as a research field of glycobiology has also been fully developed. Among them, the chemical reaction of monosaccharide is the simplest, and it is also the basis for the synthesis of glycosides (esters) and intermediates for the synthesis of glycosides (esters). 2,3,4,6-Tetra-O-acetyl-glucopyranose is an important inte...

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): C07H13/06C07H1/00C07H1/06
CPCC07H13/06C07H1/00C07H1/06
Inventor朱玉亮袁婷婷
Owner江西艾立斯特生物科技有限公司