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A method for synthesizing various glycosides based on 4-methylumbelliferone

A technology of methyl umbelliferone and glycoside, applied in the field of chemical synthesis, can solve the problems of long reaction time, difficult source, poor stereoselectivity and the like

Active Publication Date: 2018-09-28
GUANGDONG INST OF MICROBIOLOGY GUANGDONG DETECTION CENT OF MICROBIOLOGY +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0016] Looking at the above-mentioned umbelliferyl-based glycoside synthesis reports, we can find that the particularly remarkable feature of these methods is that either the precursor (such as 4-methylumbelliferyl-β-D-pyridine in Reaction Formula 7 and Reaction Formula 8 glucopyranoside) or glycosyl donors (such as acetylhalogenated sugars, which need to be synthesized from the corresponding full acetyl sugars, etc.) are not easy to source, or the stereoselectivity of the synthesis is poor and a mixture of α and β configurations is obtained at the same time , Some are also accompanied by low reaction yields (such as glycosylation reaction yield in reaction formula 1 is only 11% etc.), reaction time is too long (as in reaction formula 2, glycosylation reaction needs 3 days etc.) shortcoming

Method used

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  • A method for synthesizing various glycosides based on 4-methylumbelliferone
  • A method for synthesizing various glycosides based on 4-methylumbelliferone
  • A method for synthesizing various glycosides based on 4-methylumbelliferone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] To the 4-MU (0.264g, 1.50mmol, 1.0e.q.) and 1,2,3,4-tetra-O-acetyl-β-D-glucopyranose methyl ester (0.376g , 1.00mmol, 0.67e.q.) of dry CH 2 Cl 2 (3ml) suspension, add dry Et 3 N (525μL, 3.75mmol, 2.5e.q.), BF 3 .OEt 2 (1287μL, 10.00mmol, 6.7e.q.), stirred the reaction at room temperature for 72h, then added 3ml CH 2 Cl 2 diluted with Na 2 CO 3 solution or saturated NaHCO 3 solution to stop the reaction, then wash with dilute NaOH solution until the solution becomes light or alkaline, then wash with water and saturated saline in sequence, and wash with anhydrous NaOH after separation. 2 SO 4 The organic phase was dried, and the separated organic phase was concentrated, followed by flash column chromatography (200-300 mesh silica gel, eluted with petroleum ether II / ethyl acetate=5 / 2), and the obtained target separation liquid After removing the solvent by rotary evaporation, it was recrystallized with anhydrous ether and dried to obtain 0.084 g of white powder (...

Embodiment 2

[0044] To the 4-MU (0.264g, 1.50mmol, 1.0e.q.) and 1,2,3,4-tetra-O-acetyl-β-D-glucopyranose methyl ester (0.376g , 1.00mmol, 0.67e.q.) of dry ClCH 2 CH 2 To the Cl (3ml) suspension, add dry Et 3 N (525μL, 3.75mmol, 2.5e.q.), BF 3 .OEt 2 (1287μL, 10.00mmol, 6.7e.q.), stirred the reaction at 60°C for 5h, then added 3ml CH 2 Cl 2 diluted with Na 2 CO 3 solution or saturated NaHCO 3 solution to stop the reaction, then wash with dilute NaOH solution until the solution becomes light or alkaline, then wash with water and saturated saline in sequence, and wash with anhydrous NaOH after separation. 2 SO 4 The organic phase was dried, and the separated organic phase was concentrated, followed by flash column chromatography (200-300 mesh silica gel, eluted with petroleum ether II / ethyl acetate=5 / 2), and the obtained target separation liquid After removing the solvent by rotary evaporation, it was recrystallized with anhydrous ether and dried to obtain 0.082 g of white powder (1...

Embodiment 3

[0046] To the 4-MU (0.352g, 2.00mmol, 1.0e.q.) and 1,2,3,4-tetra-O-acetyl-β-D-glucopyranose methyl ester (0.376g , 1.00mmol, 0.50e.q.) of dry ClCH 2 CH 2 To the Cl (3ml) suspension, add dry Et 3 N (280μL, 2.00mmol, 1.0e.q.), BF 3 .OEt 2 (1287μL, 10.00mmol, 6.7e.q.), stirred the reaction under heating and reflux for 5h, then added 3ml CH 2 Cl 2 diluted with Na 2 CO 3 solution or saturated NaHCO 3 solution to stop the reaction, then wash with dilute NaOH solution until the solution becomes light or alkaline, then wash with water and saturated saline in sequence, and wash with anhydrous NaOH after separation. 2 SO 4 The organic phase was dried, and the separated organic phase was concentrated, followed by flash column chromatography (200-300 mesh silica gel, eluted with petroleum ether II / ethyl acetate=5 / 2), and the obtained target separation liquid After removing the solvent by rotary evaporation, it was recrystallized with anhydrous ether and dried to obtain 0.088 g o...

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Abstract

The invention discloses a method for synthesizing various glucosides on a basis of 4-methylumbelliferone. According to the invention, a glycosyl donor peracetyl saccharide and a glycosyl acceptor 4-methylumbelliferone are subjected to a glycosylation reaction under room temperature or under heating with dichloromethane or 1,2-dichloroethane as a solvent and with the combined effect of Lewis acid boron trifluoride ethyl ether and organic alkali triethylamine or pyridine; and protecting groups are removed, such that various glucosides based on 4-methylumbelliferone can be obtained. The glucosides include 4-methylumbelliferone-beta-D-glucopyranosiduronide, 4-methylumbelliferone-beta-D-glucopyranoside, 4-methylumbelliferone-beta-D-xylopyranoside, 4-methylumbelliferone-beta-D-ribofuranoside, 4-methylumbelliferone-alpha-D-galactopyranoside, and 4-methylumbelliferone-alpha-D-mannopyranoside. The method is simple, and can produce a beta or alpha single-configuration target. A glycosylation reaction yield can reach 17-93%.

Description

Technical field: [0001] The invention belongs to the field of chemical synthesis, and in particular relates to a method for synthesizing various glycosides based on 4-methylumbelliferone. Background technique: [0002] Glycosides based on the strong fluorescent substance 4-methylumbelliferone (4-MU; 7-hydroxy-4-methylcoumarin) can be used as glycosidase substrates, which can be used for the analysis of the corresponding glycosidase activity and the corresponding specificity Researches such as microbiological detection and human disease diagnosis where glucosidase is an important indicator. For example, 4-methylumbelliferyl-β-D-glucopyranoside is commonly used in microbial detection to detect Escherichia coli in water samples (Int. J. Food Microbiol., 2000, 60, 205-218; J. Appl.Microbiol., 2006,101,977–985), 4-methylumbelliferyl-α-D-mannopyranoside can be used as an effective and reliable diagnostic reagent for human α-mannosidosis (molecular diagnosis and Journal of Therap...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H17/075C07H1/00
CPCY02P20/55
Inventor 吴清平韦献虎马延霞张菊梅蔡芷荷卢勉飞
Owner GUANGDONG INST OF MICROBIOLOGY GUANGDONG DETECTION CENT OF MICROBIOLOGY
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