Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Synthesis method of tetrahydropyrano [3, 2-d] oxazole ring compound

A tetrahydropyran, 2-d technology, applied in the direction of organic chemistry, bulk chemical production, etc., can solve problems such as difficult to meet market demand, low target product yield, complicated process steps, etc., and achieve low production cost and high yield. The effect of high efficiency and simple process

Active Publication Date: 2020-12-29
JIANGXI NORMAL UNIV
View PDF6 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] Tetrahydropyrano[3,2-d]oxazole ring compounds are an important class of pharmaceutical compounds. At present, the industrial manufacturing cost is high, the process steps are complicated, and the yield of the target product is low, and the impurity content is high, which requires subsequent purification. , resulting in high prices, it is difficult to meet market demand

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
  • Synthesis method of tetrahydropyrano [3, 2-d] oxazole ring compound
  • Synthesis method of tetrahydropyrano [3, 2-d] oxazole ring compound
  • Synthesis method of tetrahydropyrano [3, 2-d] oxazole ring compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Such as figure 1 As indicated, add 2-acetylamino-2-deoxy-3,4,6-tri-O-benzyl-D-glucose (0.3mmol) into one-necked flask A, and add 1,1-sulfur into one-necked flask B Acyldiimidazole (1.0mmol), KF (2.0mmol), such as figure 1 As shown, the two single-necked flasks were sealed with an inversion stopper and connected with a catheter. Inject 4mL of DCM (dichloromethane) and 1.0mmol of TEA (triethylamine) into bottle A with a syringe; inject 0.3mL of TFA (trifluoroacetic acid) into bottle B, stir and react at room temperature for 20 hours, and the reaction equation is:

[0018]

[0019] (subsequent embodiment equation is similar to this, not listed in particular).

[0020] After the reaction was complete, it was spin-dried under reduced pressure and separated by silica gel column chromatography to obtain the target compound (108 mg).

[0021] Substrate: 2-Acetamido-2-deoxy-3,4,6-tri-O-benzyl-D-glucose

[0022] Target product: , yield 76%.

Embodiment 2

[0024] Such as figure 1 As indicated, add 2-acetylamino-2-deoxy-3,4,6-tri-O-benzoyl-D-glucose (0.3mmol) into one-necked flask A, and add 1,1- Sulfuryldiimidazole (1.2mmol), KF (2.4mmol), such as figure 1 As shown, the two single-necked flasks were sealed with an inversion stopper and connected with a catheter. Inject 5 mL of DCM (dichloromethane) and 1.2 mmol of TEA (triethylamine) into bottle A with a syringe; inject 0.5 mL of TFA (trifluoroacetic acid) into bottle B, and stir at 0°C for 20 hours. After the reaction was complete, it was spin-dried under reduced pressure and separated by silica gel column chromatography to obtain the target compound (98 mg).

[0025] Substrate: 2-Acetamido-2-deoxy-3,4,6-tri-O-benzoyl-D-glucose

[0026] Target product: , yield 63%.

Embodiment 3

[0028] Such as figure 1 As indicated, add 2-acetylamino-2-deoxy-3,4,6-tri-O-acetyl-D-glucose (0.3mmol) into single-necked flask A, and add 1,1-sulfur into single-necked flask B Acyldiimidazole (1.4mmol), KF (3.0mmol), such as figure 1 As shown, the two single-necked flasks were sealed with an inversion stopper and connected with a catheter. Inject 6 mL of DCM (dichloromethane) and 1.4 mmol of TEA (triethylamine) into bottle A with a syringe; inject 0.6 mL of TFA (trifluoroacetic acid) into bottle B, and stir at 10°C for 20 hours. After the reaction was complete, it was spin-dried under reduced pressure and separated by silica gel column chromatography to obtain the target compound (55 mg).

[0029] Substrate: 2-Acetamido-2-deoxy-3,4,6-tri-O-acetyl-D-glucose

[0030] Target product: , yield 55%.

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 discloses a tetrahydropyrano [3, 2d] oxazole ring compound and a synthesis method thereof.The synthesis method includes the following steps that a sealed container A and a sealed container B are designed, the tops of the two sealed containers are communicated through a guide pipe, 2-acetamido-2-deoxy-D-pyranose protected by a protecting group is added into the container A, - and 1, 1-sulfonyldiimidazole andpotassium fluoride are added into the container B, dichloromethane and triethylamine are injected into the container A, and trifluoroacetic acid is injected into the containerB, sulfuryl fluoride gas is generated in situ in the container B, the sulfuryl fluoride gas is introduced into the container A through a conduit, stirring and reacting are carried out in the containerA, reduced pressure spin-drying is carried out after the reaction is completed, and silica gel rapid column chromatography separation is carried out to obtain the target compound. The process for preparing the tetrahydropyrano [3, 2-d] oxazole ring compound is simple, the yield of the target compound is high, and the substrate range is wide. And the reaction can be carried out at normal temperature, and the method is simple, convenient to operate and suitable for conventional preparation.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, in particular to a method for synthesizing tetrahydropyrano[3,2-d]oxazole ring compounds. Background technique [0002] Tetrahydropyrano[3,2-d]oxazole ring compounds are an important class of pharmaceutical compounds. At present, the industrial manufacturing cost is high, the process steps are complicated, and the yield of the target product is low, and the impurity content is high, which requires subsequent purification. , resulting in high prices, it is difficult to meet market demand. Contents of the invention [0003] In view of the above technical problems, the present invention provides a tetrahydropyrano[3,2-d]oxazole ring compound, the general structural formula of which comprises the following two types: [0004] ; [0005] Wherein, R is selected from methyl, acetyl, pivaloyl, benzoyl, benzyl. [0006] The preparation method of the above-mentioned tetrahydropyrano[3,2-d]...

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): C07D498/04C07D498/14
CPCC07D498/04C07D498/14Y02P20/55
Inventor 范乃立胡祥国廖维林张文锋林春花
Owner JIANGXI NORMAL UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com