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

Method for synthesizing chiral purine noncyclic nucleoside through dynamic and kinetic resolution of purine, aldehyde and anhydride

A dynamic kinetics, cyclic nucleoside technology, applied in organic chemistry methods, chemical instruments and methods, asymmetric synthesis, etc., can solve the problems of difficult preparation and high cost of chiral substrates, and achieve a rich and efficient synthesis method of product structure. , the effect of easy availability of reaction raw materials

Active Publication Date: 2018-03-23
HENAN NORMAL UNIV
View PDF1 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Chiral substrates are relatively difficult to prepare and costly

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 synthesizing chiral purine noncyclic nucleoside through dynamic and kinetic resolution of purine, aldehyde and anhydride
  • Method for synthesizing chiral purine noncyclic nucleoside through dynamic and kinetic resolution of purine, aldehyde and anhydride
  • Method for synthesizing chiral purine noncyclic nucleoside through dynamic and kinetic resolution of purine, aldehyde and anhydride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024]

[0025]

[0026] Reaction conditions: 1a (0.1mmol), catalyst (10mol%), and base (10mol%) were added ina test tube, followed by adding 3a, 2a, and solvent (2mL) at room temperature. b Isolated yield based on 1a. c Determined by chiral HPLC analysis. d At 50℃. MS (60mg) was added.

[0027] In the process of screening the reaction conditions, the influence of PPY-type chiral catalysts on the reaction was first investigated (markers 1-7). At the same time, by comparing the effects of different catalysts on the reaction, the best catalyst for catalyst C7 was determined.

[0028] Investigation of reaction conditions: In a 10mL vacuum tube, add 6-chloropurine 1a (15.4mg, 0.1mmol), C7 (7.7mg, 10mol%), sodium carbonate (1mg, 0.10mmol) and acetaldehyde 2a (16μL, 0.3 mmol), acetic anhydride 3a (24 μL, 0.3 mmol). Then add 2mL of toluene, 60mg of Molecular sieve. The reaction tube was sealed, and the reaction tube was placed under a magnetic stirrer at room temperatu...

Embodiment 2

[0041]

[0042] In a 10 mL vacuum tube, add 6-chloropurine 1 (15.4 mg, 0.1 mmol), C7 (7.7 mg, 10 mol%), sodium carbonate (1 mg, 0.10 mmol) and benzaldehyde 2 (30 μL, 0.3 mmol), acetic anhydride 3 (24 μL, 0.3 mmol). Then add 2mL of toluene, 60mg of Molecular sieve. Seal the reaction tube, and place the reaction tube under a magnetic stirrer at room temperature to react for 3 days. The reaction was followed by TLC. After the reaction was terminated, the reaction solution was concentrated in vacuo, and then the target compound 4x was obtained by column chromatography. The yield was 35%, 40% ee.

Embodiment 3

[0044]

[0045] In a 10 mL vacuum tube, add 6-chloropurine 1 (15.4 mg, 0.1 mmol), C7 (7.7 mg, 10 mol%), sodium carbonate (1 mg, 0.10 mmol) and acetaldehyde 2 (16 μL, 0.3 mmol), benzyl Anhydride 3 (60mg, 0.3mmol). Then add 2mL of toluene, 60mg of Molecular sieve. Seal the reaction tube, and place the reaction tube under a magnetic stirrer at room temperature to react for 3 days. The reaction was tracked by TLC. After the reaction was terminated, the reaction solution was concentrated in vacuo, and then the target compound 4y was obtained by column chromatography with a yield of 38%, 36% ee.

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 method for synthesizing chiral purine noncyclic nucleoside through dynamic and kinetic resolution of purine, aldehyde and anhydride and belongs to the field of asymmetric synthesis in organic chemistry. Purine, aldehyde and anhydride are taken as raw materials and subjected to a catalytic reaction under catalysis of a PPY-3-acyl prolinol catalyst, and a chiral purine noncyclic nucleoside analogue is obtained. The simple, cheap and efficient synthesis method is provided for chiral noncyclic purine, raw materials for the reaction are easy to obtain, and the product hasa rich structure and high stereoselectivity.

Description

technical field [0001] The invention relates to a method for synthesizing chiral acyclic purine nucleoside analogues, in particular to a method for synthesizing chiral purine acyclic nucleosides through dynamic dynamic resolution of purine, aldehyde and acid anhydride, belonging to the field of asymmetric synthesis in organic chemistry . Background technique [0002] Chiral purine acyclic nucleoside compounds have a wide range of physiological activities. For example, Acyclovir can treat herpes simplex virus (HSV), Ganciclovir can treat cytomegalovirus (CMV), and Adefovir and Tenofovir can treat hepatitis B virus (HBV). At the same time, the product configuration of chiral compounds has a great influence on their biological activity, so the synthesis and preparation of optically pure chiral compounds and the testing and research of some physiological and pharmacological activities have great application prospects and significance . [0003] Currently, the conventional meth...

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): C07D473/40C07D473/34C07D473/38C07D473/00C07B53/00C07B57/00B01J31/02
CPCB01J31/0244C07B53/00C07B57/00C07B2200/07C07D473/00C07D473/34C07D473/38C07D473/40
Inventor 谢明胜陈阳光武晓霞渠桂荣郭海明
Owner HENAN 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