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Preparation method of 2-C-acetonyl-2-deoxy-glucoside compounds

A technology of acetylmethyl and glucoside, which is applied in the field of preparation of 2-C-acetylmethyl-2-deoxy-glucoside compounds, can solve the problems of high cost, rare reagents, environmental pollution, etc., and achieve short reaction time , less environmental pollution and high yield

Inactive Publication Date: 2009-12-02
CHENGDU INST OF BIOLOGY CHINESE ACAD OF S
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0023] The purpose of the present invention is to solve the shortcomings of high cost, rare reagents, and easy pollution to the environment in the preparation method of 2-C-alkyl substituted glucopyranoside compounds; we provide a simple, Synthetic method of 2-C-acetylmethyl-substituted glucopyranoside compounds with high yield, mild reaction conditions, good stereoselectivity and little environmental pollution

Method used

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  • Preparation method of 2-C-acetonyl-2-deoxy-glucoside compounds
  • Preparation method of 2-C-acetonyl-2-deoxy-glucoside compounds
  • Preparation method of 2-C-acetonyl-2-deoxy-glucoside compounds

Examples

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Embodiment 1

[0029] Example 1: Under nitrogen protection, 1,2-deoxy-7-C-acetyl-α-D-glucopyranose derivatives (1,R=BnO, 47mg, 0.1mmol) were added to a 5mL round bottom flask and 1,2:3,4-O-diisopropylidene-α-D-galactopyranose (26mg, 0.1mmol), add dry dichloromethane (1mL) to dissolve, then add to activate Molecular sieves (47 mg), stirred at room temperature for 1 hour, then lowered the reaction temperature to -20°C, added boron trifluoride ether (2.5 μL, 0.02 mmol), and slowly raised the temperature to react, and the reaction was detected by TLC until the end. Add an appropriate amount of triethylamine to quench the reaction, dilute the reaction system with dichloromethane (5mL), filter, and pass the filtrate through water (10mL×2), saturated aqueous sodium bicarbonate (10mL×2) and saturated brine (10mL×2) Washed and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated and purified by silica gel column chromatography (eluent: petroleum ether / ethyl acetate 3...

Embodiment 2

[0030] Example 2: Under nitrogen protection, 1,2-deoxy-7-C-acetyl-α-D-glucopyranose derivative (1,R=BnO, 59mg, 0.125mmol) was added to a 5mL round bottom flask and 1,2:3,4-O-diisopropylidene-α-D-galactopyranose (26mg, 0.1mmol), add dry dichloromethane (1mL) to dissolve, then add to activate Molecular sieves (47 mg), stirred at room temperature for 1 hour, then lowered the reaction temperature to -20°C, added boron trifluoride ether (3.2 μL, 0.025 mmol), and slowly raised the temperature to react, and the reaction was detected by TLC until the end. Add an appropriate amount of triethylamine to quench the reaction, dilute the reaction system with dichloromethane (5mL), filter, and pass the filtrate through water (10mL×2), saturated aqueous sodium bicarbonate (10mL×2) and saturated brine (10mL×2) Washed and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated and purified by silica gel column chromatography (eluent: petroleum ether / ethyl acetate ...

Embodiment 3

[0031] Example 3: Under nitrogen protection, 1,2-deoxy-7-C-acetyl-α-D-glucopyranose derivatives (1, R=BnO, 38mg, 0.08mmol) were added to a 5mL round bottom flask and 1,2:3,4-O-diisopropylidene-α-D-galactopyranose (26mg, 0.1mmol), add dry dichloromethane (1mL) to dissolve, then add to activate Molecular sieves (47mg) were stirred at room temperature for 1 hour, then the reaction temperature was lowered to -20°C, boron trifluoride ether (2.0 μL, 0.016 mmol) was added, the temperature was raised slowly, and the reaction was detected by TLC until the end. Add an appropriate amount of triethylamine to quench the reaction, dilute the reaction system with dichloromethane (5mL), filter, and pass the filtrate through water (10mL×2), saturated aqueous sodium bicarbonate (10mL×2) and saturated brine (10mL×2) Washed and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated and purified by silica gel column chromatography (eluent: petroleum ether / ethyl acet...

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Abstract

The invention belongs to the fields of organic chemistry and pharmacochemistry, in particular to a preparation method of 2-C-acetonyl-2-deoxy-glucoside compounds. The preparation method comprises the following steps: sequentially adding 1, 2-deoxy-7-C-acetyl-alpha-D-glucopyranose derivatives, receptors, such as alcohol, and solvents, such as methylene dichloride into the same reactor under the protection of nitrogen, controlling the reaction temperature between -20 DEG C and the room temperature, and adding catalysts, such as trimethylsilyl triflate to generate 2-C-acetonyl-2-deoxy-beta-D-glucopyranose compounds through reaction. The preparation method has the advantages of simple operation, mild reaction condition, good stereoselectivity and less environment pollution.

Description

technical field [0001] The invention belongs to the fields of organic chemistry and medicinal chemistry, and specifically relates to a preparation method of 2-C-acetylmethyl-2-deoxy-glucoside compounds. Background technique [0002] In organic synthesis and pharmaceutical synthesis, 2-C-alkyl substituted sugar compounds are an important class of intermediates, especially in the synthesis of active natural products and active oligosaccharides. For example, Eduardo Fernandez-Megia, Steven V.Ley, etc. in the fragment synthesis of Altohyrtin A (Synlett, 1998, 991-994) prepared 2-C-methyl-2- The key intermediate of deoxy-3,4,6-O-tribenzyl-D-glucopyranoside compounds; Danishefsky et al. in the process of synthesizing cytotoxic reagents epothilone A and B (J.Am.Chem.Soc .1997, 119, 10073-10092) also adopted 2-C-dimethyl substituted glycosides as key intermediates. According to literature reports, there are many preparation methods of 2-C-alkyl substituted D-glucopyranoside compou...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H13/02C07H5/00
Inventor 邵华武田强
Owner CHENGDU INST OF BIOLOGY CHINESE ACAD OF S
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