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Method for preparing 2-C-acetonyl-2-deoxy-D-galactopyranose and derivatives of 2-C-acetonyl-2-deoxy-D-galactopyranose

A technology for galactopyranosyl and galactopyranoside, which is applied in the preparation of sugar derivatives, sugar derivatives, sugar derivatives, etc., can solve the problems of high cost, rare reagents, environmental pollution, etc., and achieves low cost and high reaction efficiency. Short time and less environmental pollution

Inactive Publication Date: 2011-05-25
CHENGDU INST OF BIOLOGY CHINESE ACAD OF S
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0031] 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 galactose and its derivatives; Preparation method of 2-C-acetylmethyl-2-deoxy-D-galactopyranose and its derivatives with short time, high yield, low cost and less environmental pollution

Method used

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  • Method for preparing 2-C-acetonyl-2-deoxy-D-galactopyranose and derivatives of 2-C-acetonyl-2-deoxy-D-galactopyranose
  • Method for preparing 2-C-acetonyl-2-deoxy-D-galactopyranose and derivatives of 2-C-acetonyl-2-deoxy-D-galactopyranose
  • Method for preparing 2-C-acetonyl-2-deoxy-D-galactopyranose and derivatives of 2-C-acetonyl-2-deoxy-D-galactopyranose

Examples

Experimental program
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Effect test

Embodiment 1

[0054] Example 1: Under the protection of Ar, add 1,2-deoxy-3,4,6-tri-O-benzyl-7-C-acetyl-α-D-galactopyranose to a 5mL round bottom flask (47.2mg, 0.1mmol) and 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose (28.2mg, 0.11mmol), then add dry dichloromethane (1mL) dissolved, then activated by adding Molecular sieves (47mg), stirred at room temperature for 30 minutes, the reaction temperature dropped to -20°C, added boron trifluoride ether (2.5μL, 0.02mmol), and then the temperature was slowly raised to react, and the reaction was detected by TLC until the end. Add an appropriate amount of triethylamine to quench the reaction, then add dichloromethane (5mL) to dilute the reaction system, filter, and pass the filtrate through water (10mL×2), saturated aqueous sodium bicarbonate (10mL×2) and saturated saline (10mL×2) 2) Washing and drying over anhydrous sodium sulfate. After filtration, the filtrate was concentrated and purified by silica gel column chromatography (eluent: petro...

Embodiment 2

[0055] Example 2: Under the protection of Ar, add 1,2-deoxy-3,4,6-tri-O-benzyl-7-C-acetyl-α-D-galactopyranose to a 5mL round bottom flask (47.2mg, 0.1mmol) and 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose (28.2mg, 0.11mmol), then add dry ether (1mL) to dissolve, reactivation Molecular sieves (47mg) were stirred at room temperature for 30 minutes, the reaction temperature was lowered to -20°C, and boron trifluoride ether (2.5μL, 0.02mmol) was added, and then the temperature was slowly raised to react, and the reaction was detected by TLC until the end. Add an appropriate amount of triethylamine to quench the reaction, then add dichloromethane (5mL) to dilute the reaction system, filter, and filter the filtrate through water (10mL×2), saturated aqueous sodium bicarbonate (10mL×2) and saturated brine (10mL×2 ) and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated and purified by silica gel column chromatography (eluent: petroleum ether / eth...

Embodiment 3

[0056] Example 3: Under the protection of Ar, add 1,2-deoxy-3,4,6-tri-O-benzyl-7-C-acetyl-α-D-galactopyranose to a 5mL round bottom flask (47.2mg, 0.1mmol) and 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose (28.2mg, 0.11mmol), followed by the addition of dry dichloromethane (1mL) dissolved, then added to activate Molecular sieves (47mg), stirred at room temperature for 30 minutes, the reaction temperature dropped to -20°C, trimethylsilyl trifluoromethanesulfonate (4.0μL, 0.04mmol) was added, and then the temperature was slowly raised to react, and the reaction was detected by TLC until the end. Add an appropriate amount of triethylamine to quench the reaction, then add dichloromethane (5mL) to dilute the reaction system, filter, and pass the filtrate through water (10mL×2), saturated aqueous sodium bicarbonate (10mL×2) and saturated brine (10mL×2 ) and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated and purified by silica gel column chr...

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Abstract

The invention belongs to the technical field of organic chemistry and pharmaceutical chemistry, and particularly relates to a method for preparing 2-C-acetonyl-2-deoxy-D-galactopyranose and derivatives of the 2-C-acetonyl-2-deoxy-D-galactopyranose. In the method, a 1,2-deoxy-7-C-acetyl-alpha-D-galactopyranose derivative reacts with glycosylated acceptors of alcohol, thioalcohol, amino acid derivatives, monosaccharide derivatives and the like in the presence of one of trimethylsilyl trifluoromethanesulfonate, boron trifluoride ether, anhydrous aluminum trichloride, anhydrous bismuth trichloride and anhydrous zinc chloride to generate the 2-C-acetonyl-2-deoxy-D-galactopyranose and the derivatives thereof. The method has the advantages of mild reaction condition, good reaction selectivity, high yield and the like.

Description

technical field [0001] The invention belongs to the technical field of organic chemistry and medicinal chemistry, and specifically relates to a method for preparing 2-C-acetylmethyl-2-deoxy-D-galactopyranose and derivatives thereof. Background technique [0002] Oligosaccharide metabolism engineering uses 2-C-acetylmethyl-2-deoxy-D-galactopyranose as a structural analog of 2-acetylamino-2-deoxy-D-galactopyranose to study cell surface oligosaccharides and sugars Biosynthesis and structure / function relationships of conjugates (J.Am.Chem.Soc. 2001, 123, 1242-1243; J.Am.Chem.Soc. 2003, 125, 16162-16163.). The Qasba group used chemical enzymatic methods to study the positioning and characterization of 2-C-acetylmethyl-2-deoxy-D-galactopyranose and biological macromolecules such as cell surface antigens, monoclonal antibodies, proteins, and glycans. This study affirmed the potential medicinal value and biological research significance of 2-C-acetylmethyl-2-deoxy-D-galactopyranose...

Claims

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Application Information

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IPC IPC(8): C07H1/00C07H9/04C07H15/18C07H15/04C07H15/24C07H15/14
Inventor 邵华武田强
Owner CHENGDU INST OF BIOLOGY CHINESE ACAD OF S
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