Method for synthesis of chiral heterocyclic nucleoside analogue by asymmetric [3+2] cycloaddition

A nucleoside analog and cycloaddition technology, applied in the fields of chemistry and medicine, can solve the problems of complex process and expensive raw materials, and achieve the effects of simple operation, easy-to-obtain catalyst, and concise and practical synthesis method.

Inactive Publication Date: 2015-05-06
HENAN NORMAL UNIV
View PDF0 Cites 14 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Seeking a simple, green and efficient asymmetric cycloaddition method to synthesize chiral cyclic nucleoside analogs, based on solving the problems of expensive raw materials and complicated processes in

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 synthesis of chiral heterocyclic nucleoside analogue by asymmetric [3+2] cycloaddition
  • Method for synthesis of chiral heterocyclic nucleoside analogue by asymmetric [3+2] cycloaddition
  • Method for synthesis of chiral heterocyclic nucleoside analogue by asymmetric [3+2] cycloaddition

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] The asymmetric cycloaddition reaction formula provided by the present invention is as follows:

[0029]

[0030] Take a Shurank tube, under the protection of nitrogen, with 1mol% Cu(CH 3 CN 4 )ClO 4 and 1 mol% of ligand L in freshly distilled CH 2 Cl 2 As a solvent, it was stirred at room temperature for 30 min, and then the imine substrate (0.3 mmol), dipolarophile (0.36 mmol) and 2 mg of potassium carbonate were sequentially added. React at minus 25 degrees Celsius. Through thin-layer plate detection (TLC); through column chromatography, the target product was obtained with a yield of 95% and ee>99%.

[0031] 1 H NMR (400MHz, CDCl 3 ): δ8.77(s, 1H), 8.40(s, 1H), 7.60(d, J=7.2Hz, 2H), 7.42-7.32(m, 3H), 5.83(dd, J=7.2Hz, 6.0Hz , 1H), 4.52(d, J=8.8Hz, 1H), 4.47(d, J=7.2Hz, 1H), 4.20-4.07(m, 2H), 3.53(dd, J=8.8Hz, 5.6Hz, 1H ), 3.33(s, 3H), 3.11(s, 1H), 1.14(t, J=7.2Hz, 3H). 13 C NMR (100MHz, CDCl 3 ): δ170.9, 169.1, 152.0, 151.7, 151.4, 144.5, 139.2, 131.4, ...

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 synthesis of a chiral heterocyclic nucleoside analogue by asymmetric [3+2] cycloaddition. A reaction equation is shown in the following description. Through use of a specific chiral catalyst, high-yield and high-enantiomer excess value chiral product production is realized. The method has the advantages of simple operation, mild reaction condition, cheap and easily available catalyst, and gram-scale reaction feasibility and provides a simple and practical synthesis method of the chiral heterocyclic nucleoside analogue.

Description

Technical field: [0001] The invention belongs to the technical field of chemistry and medicine, and in particular relates to a method for obtaining chiral heterocyclic nucleoside analogs through an asymmetric [3+2] cycloaddition reaction. Background technique: [0002] Nucleoside drugs play a very important role in antiviral and antitumor chemotherapy drugs, especially in the past ten years, the development of drugs in this area is very fast. The structural modification of natural nucleosides is an important means to find new and more effective antiviral drugs. Among the antiviral drugs currently on the market and in clinical trials, most of them are nucleoside derivatives. Nucleoside derivatives therefore become the compounds with the most antiviral potential. However, such drugs still generally have many adverse reactions, low bioavailability, easy to produce drug resistance, fast metabolism and other problems. Therefore, it is of great significance to modify various par...

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): C07D473/40C07D473/00C07D473/30C07D473/34C07D473/38C07D403/04
CPCC07D473/40C07D403/04C07D473/00C07D473/30C07D473/34C07D473/38
Inventor 郭海明杨启亮谢明胜王东超王海霞渠桂荣
Owner HENAN NORMAL 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