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Preparation method of full benzyl protection beta-aromatic oxygen glucoside

A technology of aryl oxyglycosides and benzyl, which is applied in the field of preparation of all-benzyl protected β-aryl oxyglycosides, can solve the problems of easy rearrangement of products, expensive catalysts, cumbersome operation steps, etc., and avoid high toxicity The use of chemical raw materials, the wide application range of substrates and the effect of simple process

Inactive Publication Date: 2014-05-28
EAST CHINA NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Glucose, galactose, and xylose β-aryloxyglycoside products produced by the prior art have high donor toxicity or poor stability, expensive and toxic catalysts, and products are prone to rearrangement, and the yield is low and There are by-products in α configuration, and the operation steps are cumbersome, which seriously affects the wide application of glucose, galactose, and xylose β-aryloxyglycoside products

Method used

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  • Preparation method of full benzyl protection beta-aromatic oxygen glucoside

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] (1), preparation of solid acid catalyst

[0018] Take 1 gram of FeCl 3 (Chemical pure) mixed with 4 grams of activated carbon evenly, dissolved in 10mL ethanol (chemical pure), heated and refluxed for 10min, the reflux temperature was 85°C, and then the ethanol was removed by vacuum rotary evaporation at a pressure of 850KPa, and then dried at 120°C 1.5 hours, produced FeCl 3 / C solid acid catalyst.

[0019] (2), glycosylation reaction

[0020] Under nitrogen protection, take 58 mg 2,3,4,6-tetra- O -Benzyl-D-glucose propynyl glycoside (0.1003 mmol) and 23 mg p-tert-butylphenol (0.15 mmol) were added to the flask, followed by 5 mL of anhydrous acetonitrile, followed by FeCl 3 / C solid acid catalyst 10 mg, heat up to 60 o C, Stir the reaction, TLC plate tracking and monitoring the reaction (PE:EA=10:1), after 6 hours, TLC monitors that the reaction of the raw materials is complete, filter out the catalyst, and the filtrate is concentrated and purified to obtain the p...

Embodiment 2

[0026] (1), preparation of solid acid catalyst

[0027] Take 1 gram of FeCl 3 (Chemically pure) mixed with 8 grams of activated carbon evenly, dissolved in 12mL ethanol (chemically pure), heated and refluxed for 20min, the reflux temperature was 89°C, and then the ethanol was removed by vacuum rotary evaporation at a pressure of 750KPa, and then dried at 105°C 1 hour, made FeCl3 / C solid acid catalyst.

[0028] (2), glycosylation reaction

[0029] Under nitrogen protection, take 46 mg 2,3,4-tri- O -Benzyl-D-xylopropynyl glycoside (0.1004 mmol) and p-17 mg methylphenol (0.15 mmol) were added to the flask, and then 5 mL of anhydrous acetonitrile was added, followed by FeCl 3 / C solid acid catalyst 10 mg, heat up to 60 oC, Stir the reaction, TLC plate tracking and monitoring the reaction (PE:EA=10:1), after 6 hours, TLC monitors that the reaction of the raw materials is complete, filter out the catalyst, and the filtrate is concentrated and purified to obtain the product 2,3,4...

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Abstract

The invention discloses a preparation method of full benzyl protection beta-aromatic oxygen glucoside, which is characterized in that full benzyl propargyl glucoside is mixed with acetonitrile, methylene dichloride, chloroform, diethyl ether, dioxane or tetrahydrofuran according to the molar volume ratio of 1 mol : (10-100) L, a phenol receptor is added under agitating, synthetic reaction of the full benzyl protection beta-glycol glucoside is carried out under the action of a FeC13 / C solid acid catalyst and at the temperature of 20-100 DEG C, and a filtrate is concentrated and purified after the reaction to obtain the full benzyl protection beta-aromatic oxygen glycoside, wherein the equivalence ratio of the phenol receptor to propargyl alcohol glycoside is (1.0-5.0) : 1. Compared with the conventional method, the preparation method has the advantages of simple process, convenience in operation, wide substrate applicable scope, high yield, good stereoselectivity, low production cost and milder reaction conditions, and the use of highly-toxic chemical raw materials is avoided. The preparation method is a new preparation method of the full benzyl protection beta-aromatic oxygen glucoside, which is environmentally-friendly, economic and efficient and has a good application prospect.

Description

technical field [0001] The invention relates to the technical field of synthesis of pharmaceutical intermediates, in particular to a method for preparing all benzyl protected β-aryl oxyglycosides. Background technique [0002] The high-efficiency stereoselective synthesis of aryl oxyglycosides has always been a difficult problem, mainly for the following reasons: first, compared with aliphatic alcohols, the electron-withdrawing nature of the aromatic ring itself, under acidic conditions, phenolic compounds The nucleophilicity of the acceptor is lower than that of aliphatic alcohols; secondly, the generated aryl oxyglycosides are easily rearranged into the corresponding aryl carbonic glycosides, and a certain amount of by-products are introduced; Phenolic compounds with large steric hindrance cannot undergo glycosylation reaction. At present, the preparation methods of glucose, galactose, and xylose β-aryloxyglycosides are mainly divided into two categories: the first catego...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H15/203C07H1/00
Inventor 张剑波司文帅李娟骆小胜
Owner EAST CHINA NORMAL UNIV