Eureka AIR delivers breakthrough ideas for toughest innovation challenges, trusted by R&D personnel around the world.

Method for stereoselective preparation of derivatives of pyrane

A technology of pyran derivatives and stereoselectivity, which is applied to the preparation of sugar derivatives, sugar derivatives, and sugar derivatives. It can solve the problems of rare reagents, environmental pollution, and high cost, and achieve low environmental pollution and high selectivity. High and low cost effect

Inactive Publication Date: 2011-09-14
CHENGDU INST OF BIOLOGY CHINESE ACAD OF S
View PDF0 Cites 4 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0034] The purpose of the present invention is to solve the disadvantages of high cost, rare reagents and easy pollution to the environment in the preparation method of pyran derivatives; we provide a method with simple operation, short reaction time, high yield and stereoselectivity Preparation method of pyran derivatives with good quality, lower cost and less environmental pollution

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 stereoselective preparation of derivatives of pyrane
  • Method for stereoselective preparation of derivatives of pyrane
  • Method for stereoselective preparation of derivatives of pyrane

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] Example 1: Under Ar protection, 1-ethylthio-2-C-acetaldehyde-α-D-glucopyranose derivatives 2 (52 mg, 0.1 mmol) and 2,3 were added to a 5 mL round bottom flask -O-isopropylidene-α-L-rhamnopyranoside (26.2mg, 0.12mmol), then add dry dichloromethane (2mL) to dissolve, then add to activate Molecular sieves (50 mg), stirred at room temperature for 30 minutes, the reaction temperature dropped to -30 ° C, added NIS (33.8 mg, 0.15 mmol), and then added trimethylsilyl trifluoromethanesulfonate (9.0 μ L, 0.05 mmol) Slowly heat up the reaction, and TLC detects that the reaction is complete. Add an appropriate amount of sodium thiosulfate to quench the reaction, then add dichloromethane (5mL) to dilute the reaction system, filter, the filtrate is washed with water (10mL×2), saturated brine (10mL×2), and then washed with anhydrous sodium sulfate dry. After filtration, the filtrate was concentrated and purified by silica gel column chromatography (eluent: petroleum ether / ethyl ace...

Embodiment 2

[0058] Example 2: Under Ar protection, 1-ethylthio-2-C-acetaldehyde-α-D-glucopyranose derivatives 2 (52 mg, 0.1 mmol) and 2,3 were added to a 5 mL round bottom flask -O-isopropylidene-α-L-rhamnopyranoside (26.2mg, 0.12mmol), then add dry dichloromethane (2mL) to dissolve, then add to activate Molecular sieves (50mg), stirred at room temperature for 30 minutes, the reaction temperature dropped to -30°C, NIS (33.8mg, 0.15mmol) was added, and silver trifluoromethanesulfonate (12.8mg, 0.05mmol) was added, and then the temperature was slowly raised to react. TLC detection reaction was completed. Add an appropriate amount of sodium thiosulfate to quench the reaction, then add dichloromethane (5mL) to dilute the reaction system, filter, the filtrate is washed with water (10mL×2), saturated brine (10mL×2), and then washed with anhydrous sodium sulfate dry. After filtration, the filtrate was concentrated and purified by silica gel column chromatography (eluent: petroleum ether / ethyl...

Embodiment 3

[0059] Example 3: Under Ar protection, 1-ethylthio-2-C-acetaldehyde-α-D-glucopyranose derivatives 2 (52 mg, 0.1 mmol) and 2,3 were added to a 5 mL round bottom flask -O-isopropylidene-α-L-rhamnopyranoside (26.2mg, 0.12mmol), then add dry dichloromethane (2mL) to dissolve, then add to activate Molecular sieves (50mg), stirred at room temperature for 30 minutes, the reaction temperature dropped to -30°C, NIS (33.8mg, 0.15mmol) was added, and trifluoromethanesulfonic acid (2.2μL, 0.025mmol) was added, then the temperature was slowly raised to react, TLC Detection reaction to the end. Add an appropriate amount of sodium thiosulfate to quench the reaction, then add dichloromethane (5mL) to dilute the reaction system, filter, the filtrate is washed with water (10mL×2), saturated brine (10mL×2), and then washed with anhydrous sodium sulfate dry. After filtration, the filtrate was concentrated and purified by silica gel column chromatography (eluent: petroleum ether / ethyl acetate =...

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 belongs to the technical field of organic chemistry and pharmaceutical chemistry, and in particular relates to a method for stereoselective preparation of derivatives of pyrane. The method comprises the following steps of: under the protection of inert gases, adding derivatives of 1-p-tolylthio-2-C-glyoxyl-alpha-D-glucopyranose, derivatives of 1-thiophenyl-2-C- glyoxyl-alpha-D-glucopyranose or derivatives of 1-ethylthio p-tolyl-2-C-glyoxyl-alpha-D-glucopyranose, which serve as reactants, into a reactor, adding alcohol, phenol, trimethylsilyl azide or monosaccharide derivatives, adding a solvent such as methylene chloride to dissolve the raw materials, and performing the reaction at the reaction temperature of between 40 DEG C below zero and room temperature in the presence of a catalyst which is N-iodosuccinimide, or N-bromosuccinimide, or copper bromide and tetrabutylammonium bromide, or iodine, bromine simple substance or N-iodosuccinimide and trimethylsilyl triflate, or trifluoromethanesulfonic silver, or paratoluenesulfonic acid or trifluoromethanesulfonic acid to obtain the derivatives of pyrane. The method has the advantages of simple operation, high selectivity, low cost, light environmental pollution and the like.

Description

technical field [0001] The invention belongs to the technical field of organic chemistry and medicinal chemistry, and in particular relates to a method for stereoselectively preparing pyran derivatives. Background technique [0002] Pyran derivatives exist in many natural product compounds with important biological activities, such as tetrahydroaplysul-phurin (J.Nat.Prod.2009, 72, 1471-1476); ovaxenicins A (Nat.Prod.Rep.2007, 24, 1332-1341); penifulvin A, B, C (Org.Lett.2010, 12, 272-275); Azadirachtin (Angew.Chem., Int.Ed.2007, 46, 7629-7632.; Angew.Chem ., Int.Ed.2007, 46, 7633-7635; Chem.-Eur.J.2008, 14, 10683-10704), cadlinolide A, B. (J.Org.Chem.1991, 56, 42-47) . Among these compounds, azadirachtin has attracted much attention as a new plant-derived insecticide with high efficiency and low toxicity (National Researchcouncil: Neem: A tree solving global problems [A] Washington D.C.: National Academy Press.1992, PP: 6 -37; J.Nat.Prod.2005, 68, 1047-1050; J.Agric.Food ...

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): C07H19/01C07H1/00A01N43/90A01P7/00
Inventor 邵华武马小锋
Owner CHENGDU INST OF BIOLOGY CHINESE ACAD OF S
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
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