Synthesizing method of n-alkyl-beta-D-glucopyranoside

A technology of glucopyranoside and fully acetylated glucopyranose, applied in the field of synthesis of n-alkyl-β-glucoside, which can solve the problems of physical injury to experimenters, unavoidable environmental pollution, cumbersome preparation process, etc. Effects of low cost, reduced bodily harm, and simplified synthesis process

Inactive Publication Date: 2015-11-11
天津市益科司德科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This method uses precious metal silver, and the amount of silver is relatively large, and the price of silver salt is relatively high and difficult to preserve, resulting in high cost and complicated preparation process, and the price of 2,3,4,6‐tetraacetyl bromoglucose is also high. Relatively expensive, the industrial preparation of 2,3,4,6‐tetraacetylbromoglucose requires the use of hydr

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  • Synthesizing method of n-alkyl-beta-D-glucopyranoside
  • Synthesizing method of n-alkyl-beta-D-glucopyranoside

Examples

Experimental program
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Example Embodiment

[0024] Example 1

[0025] A synthetic method of n-octyl-β-D-glucopyranoside, comprising the steps:

[0026] 1) Weigh (200g, 0.51mol) peracetylated glucopyranose and dissolve it in 1L of anhydrous dichloromethane, and add n-octanol (66.7g, 0.51mol), add 0.51mol of anhydrous tin tetrachloride, The reaction was stirred at room temperature for 30 minutes, washed with 500ml*3 saturated aqueous sodium carbonate solution, the organic phase was collected, and distilled under reduced pressure to obtain light yellow oily 1-n-octyl-2,3,4,6-tetraacetyl-β-D- glucopyranoside;

[0027] 2) Dissolve 237 g of the obtained 1-n-octyl-2,3,4,6-tetraacetyl-β-D-glucopyranoside in 1.2L methanol, stir at room temperature, and add sodium methoxide to adjust the pH To 9, react at room temperature for 1.5 hours, adjust to neutrality with strongly acidic cation exchange resin Dowex-509, filter, and spin dry the filtrate to obtain n-octyl-β-D-glucopyranoside (81.9g, 0.28mol) , the yield was 55%, and the ...

Example Embodiment

[0029] Example 2

[0030] A synthetic method of n-dodecyl-β-D-glucopyranoside, comprising the steps:

[0031] 1) Dissolve peracetylated glucopyranose, n-dodecyl alcohol and anhydrous tin tetrachloride in anhydrous dichloromethane, stir the reaction at room temperature for 20 minutes, wash with saturated aqueous potassium carbonate solution, collect the organic phase, Under reduced pressure distillation to obtain 1-n-dodecyl-2,3,4,6-tetraacetyl-β-D-glucopyranoside;

[0032] The molar ratio of peracetylated glucopyranose, n-dodecyl alcohol and anhydrous tin tetrachloride is: 1:1.2:1.2;

[0033] The ratio of peracetylated glucopyranose to anhydrous dichloromethane is 100g:550ml;

[0034] 2) Dissolve 1-n-dodecyl-2,3,4,6-tetraacetyl-β-D-glucopyranoside in methanol, add sodium methoxide to adjust pH to 9, and react at room temperature for 1.5 hours, Adjusted to neutrality with strong acid cation exchange resin Dowex-509, filtered, the filtrate was evaporated to solvent, dried, an...

Example Embodiment

[0037] Example 3

[0038] A synthetic method of n-nonyl-β-D-glucopyranoside, comprising the steps:

[0039] 1) Dissolve peracetylated glucopyranose, n-nonyl alcohol and anhydrous tin tetrachloride in anhydrous dichloromethane, stir the reaction at room temperature for 70 minutes, wash with saturated aqueous sodium bicarbonate solution, collect the organic phase, reduce Pressure distillation to obtain 1-n-nonyl-2,3,4,6-tetraacetyl-β-D-glucopyranoside;

[0040] The molar ratio of peracetylated glucopyranose, n-nonyl alcohol and anhydrous tin tetrachloride is: 1:1.1:1;

[0041] The ratio of peracetylated glucopyranose to anhydrous dichloromethane is 100g:450ml;

[0042] 2) Dissolve 1-n-nonyl-2,3,4,6-tetraacetyl-β-D-glucopyranoside in methanol, add sodium methoxide to adjust the pH to 9, react at room temperature for 1.5 hours, use strong The acidic cation exchange resin HCRW-20 was adjusted to neutrality, filtered, and the filtrate was evaporated to remove the solvent, dried, ...

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Abstract

The invention discloses a synthesizing method of n-alkyl-beta-D-glucopyranoside. The method includes the following steps of dissolving fully-acetylated glucopyranose, n-alkyl alcohol and anhydrous stannic chloride in anhydrous methylene dichloride, stirring the mixture to have a reaction for 20 min to 70 min at the room temperature, washing the mixture through a saturated sodium carbonate solution, collecting organic phases, conducting reduced pressure distillation to obtain 1-n-alkyl-2,3,4,6-tetraacetyl-beta-D-glucopyranoside, dissolving the 1-n-alkyl-2,3,4,6-tetraacetyl-beta-D-glucopyranoside in methyl alcohol, adding sodium methylate to adjust the pH value to 9, having a reaction for 1.5 h at the room temperature, adjusting the pH value to be neutral through strong acid cation exchange resin, conducting filtering, steaming filtrate to obtain solvent, and drying the solvent to obtain the n-alkyl-beta-D-glucopyranoside. The n-alkyl is n-alkyl of C8-C12. The method is simple, raw materials are easy to obtain, cost is low, reaction temperature is moderate and easy to control, the method is environmentally friendly, and the prepared beta-configuration glucopyranoside is high in purity.

Description

technical field [0001] The invention relates to a method for synthesizing n-alkyl-β-glucoside, which belongs to the field of sugar chemistry, in particular to a method for synthesizing n-alkyl-β-D-glucopyranoside. Background technique [0002] Sugars are an important class of organic substances widely distributed in nature. They are also called carbohydrates. They are the general term for polyhydroxy aldehydes or polyhydroxy ketones and their polycondensates and certain derivatives. They are generally composed of three elements: carbon, hydrogen, and oxygen. . Sugars are mainly divided into four categories: monosaccharides, disaccharides, oligosaccharides and polysaccharides. Sugar is the most important energy source for the human body, and 70% of the energy required for material transportation in the body comes from sugar. At present, more researches are monosaccharides and disaccharides. [0003] Glycosides, also known as glycosides. The hemiacetal hydroxyl group of mo...

Claims

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Application Information

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IPC IPC(8): C07H15/04C07H1/00
Inventor 赵向帅徐志浩
Owner 天津市益科司德科技有限公司
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