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Method for deacylation with hydroxyl ion type alkali as catalyst

A deacylation and hydroxide technology, applied in chemical instruments and methods, organic chemistry, sugar derivatives, etc., can solve problems such as inconvenience, and achieve the effects of simple operation, mild reaction and low price

Inactive Publication Date: 2014-10-15
HUAZHONG UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This is very inconvenient for removing cations by ion exchange after the reaction

Method used

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  • Method for deacylation with hydroxyl ion type alkali as catalyst
  • Method for deacylation with hydroxyl ion type alkali as catalyst
  • Method for deacylation with hydroxyl ion type alkali as catalyst

Examples

Experimental program
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Effect test

example 1

[0019] Example 1 reaction solvent is methyl alcohol, and catalyzer is sodium hydroxide:

[0020] Weigh 10 g of pentaacetylated glucose, dissolve it in 100 ml of normal methanol, and add 20 mg of sodium hydroxide. The reaction was stirred at room temperature for one hour. After adding 300 mg of hydrogen ion acidic resin for complete neutralization to neutrality, the resin was filtered off, and the solvent was directly evaporated to dryness under reduced pressure to obtain 4.5 g of white powder, which was shown to be pure glucose by NMR analysis, with a yield of 97.5%. Its NMR spectrum data are: 1 H NMR (400MHz,D 2 O):5.23(1H,d,H-1),3.81-3.87(2H,m,H-5,H-6b),3.73-3.79(1H,m,H-6a),3.72(1H,dd, H-3), 3.54(1H, dd, H-2), 3.42(1H, t, H-4).

example 2

[0021] Example 2 reaction solvent is methyl alcohol, and catalyzer is potassium hydroxide:

[0022] Weigh 10 g of pentaacetylated glucose, dissolve it in 100 ml of normal methanol, and add 30 mg of potassium hydroxide. The reaction was stirred at room temperature for one hour. Add 300 mg of hydrogen ion acidic resin to neutralize completely to neutrality, filter off the resin, and directly evaporate the solvent under reduced pressure to obtain 4.55 g of pure glucose in the form of white powder, with a yield of 98.6%.

example 3

[0023] Example 3 sodium hydroxide is catalyst desulfurization acetyl group:

[0024] Weigh 10 g of tetraacetylated mannose protected by the 1-thioacetyl group, dissolve it in 100 ml of ordinary methanol, and add 1.1 g of sodium hydroxide (0.2 mol / mol acyl group). The reaction was stirred at room temperature for one hour. After adding about 1 gram of hydrogen ion acidic resin for complete neutralization to neutrality, the resin was filtered off, and the solvent was directly evaporated to dryness under reduced pressure to obtain 4.8 grams of white powder, which was shown to be pure 1-mercaptomannose by nuclear magnetic analysis, with a yield of 99%. Its NMR spectrum data are: 1 H NMR (400MHz,MeOD):5.51(1H,d,H-1),4.05(1H,dd,H-3),3.92(1H,dd,H-2),3.69-3.85(3H,m,H -5,H-6,H-6'),3.65(1H,t,H-4),2.34(1H,d,SH).

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PUM

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Abstract

The invention provides a method for deacylation with a hydroxyl ion type alkali as the catalyst. The method includes: dissolving an organic compound containing one or over two acyl protecting hydroxyls in an appropriate amount of an alcohol solvent, and adding a catalytic amount of the hydroxyl ion type alkali or any other medium-strong alkali, especially hydroxyl ion type resin to undergo reaction for enough time under an appropriate temperature, thus removing acyl from the hydroxyls.

Description

technical field [0001] The invention belongs to the field of basic organic chemical industry, and the related deacylation method is widely used in laboratories and industrial devices. Background technique [0002] In organic synthesis technology, selective protection / deprotection is often an important and commonly used technique for reactants with multiple similar reactive sites. The acyl group is one of the most commonly used protecting groups because it is easy to protect and remove. The commonly used Zmplen method for deacylation has become a standard method in the industry (Zempl'en, G. and Kuntz, A., Ber., 1924, 57B, 1357; Zemple'n, G.; Pacsu, E.Ber. Dtsch. Chem. Ges. 1929, 62, 1613). The specific method is to use a catalytic amount of sodium methoxide or sodium ethoxide in methanol or ethanol solution to cause an acyl exchange reaction on the acyl-protected substrate, thereby almost completely removing the acyl group (Garc'1a-L'opez, J.J.; Hern 'andez-Mateo, F.; Isa...

Claims

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Application Information

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IPC IPC(8): C07H1/00C07H3/02C07H5/10C07H15/04
Inventor 董海任博
Owner HUAZHONG UNIV OF SCI & TECH
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