Method for stereoselective preparation of derivatives of pyrane

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

Inactive Publication Date: 2014-09-17
CHENGDU INST OF BIOLOGY CHINESE ACAD OF S
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  • Abstract
  • Description
  • Claims
  • Application Information

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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

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  • 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

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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, and 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 aceta...

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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

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H19/01C07H1/00A01N43/90A01P7/00
Inventor 邵华武马小锋
Owner CHENGDU INST OF BIOLOGY CHINESE ACAD OF S
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