Benzylation method for monosaccharide glucoside

A monosaccharide IV, benzylation technology, applied in the field of chemistry, can solve the problems of unstable solvent, increased by-product toluene, limited temperature range, etc., and achieve the effects of simplifying post-processing operations, reducing sodium hydride, and reducing pollution

Active Publication Date: 2015-12-16
浙江合糖科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] The technical problem to be solved by the present invention is: the proportion of toluene in the solvent used in the prior art is constantly increasing during the mechanical application process, which affects the process stability; and benzyl chloride or benzyl bromide to generate dibenzyl ether as a by-product; or the solvent used has a low boiling poi

Method used

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  • Benzylation method for monosaccharide glucoside
  • Benzylation method for monosaccharide glucoside
  • Benzylation method for monosaccharide glucoside

Examples

Experimental program
Comparison scheme
Effect test

Example Embodiment

[0039] Example one

[0040] Methyl-2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside

[0041] In a 250ml three-necked flask equipped with a stirrer, a thermometer and a condenser, 9.7g (50.0mmol) of methyl-α-D-glucopyranoside, sodium hydride paraffin oil dispersion (sodium hydride content 55wt%) 9.16g (209.9mmol), 60ml of toluene, 27.85g (220.0mmol) of benzyl chloride, heated to about 105-110°C, followed by liquid chromatography, and kept until the reaction is complete. After the heat preservation reaction is completed, cool down to about 60°C, slowly add water dropwise, and react with residual sodium hydride until no bubbles are formed. The solid matter was removed by filtration, and the filter cake was washed with 15 ml×2 times of toluene, and the organic layers were combined. The organic layer is heated to 65-70°C, washed with water until neutral, 20ml of water each time, washed with water for 3 to 4 times (the first washing water is discarded, and the other washing water is applied ...

Example Embodiment

[0042] Example two

[0043] Methyl-2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside

[0044] In a 250ml three-necked flask equipped with a stirrer, a thermometer, and a condenser, add 9.7g (50.0mmol) of methyl-α-D-glucopyranoside and sodium hydride paraffin oil dispersion (sodium hydride content 55%) in sequence 9.16g (209.9mmol), 60ml of toluene, 26.56g (210.0mmol) of benzyl chloride, heated to about 90-95°C, followed by liquid chromatography, and kept until the reaction is complete. After the heat preservation reaction is completed, cool down to about 60°C, slowly add water dropwise, and react with residual sodium hydride until no bubbles are formed. The solid matter was removed by filtration, and the filter cake was washed with 15 ml×2 times of toluene, and the organic layers were combined. The organic layer is heated to 65-70°C, washed with water until neutral, 20ml of water each time, washed with water for 3 to 4 times (the first washing water is discarded, and the other washing w...

Example Embodiment

[0045] Example three

[0046] Methyl-2,3,4,6-tetra-O-benzyl-α-D-galactopyranoside

[0047] In a 250ml three-necked flask equipped with a stirrer, a thermometer and a reflux trap (equipped with a condenser), add 10.6g (50.0mmol) of methyl-α-D-galactopyranoside monohydrate and toluene in sequence 100ml, heated to 90~95℃, controlled the vacuum degree -0.03~-0.04Mpa, refluxed and separated water to remove the crystal water in methyl-α-D-galactopyranoside monohydrate. After dehydration, cool to 35-40℃, and change the reflux water separator to reflux condenser. Add 10.0 g (229.2 mmol) of sodium hydride paraffin oil dispersion (content 55%) and 30.5 g (240.9 mmol) of benzyl chloride in sequence, heat to about 90-95°C, follow by liquid chromatography, and keep warm until the reaction is complete. After the heat preservation reaction is completed, cool down to about 60°C, slowly add water dropwise, and react with residual sodium hydride until no bubbles are formed. The solid matter was r...

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Abstract

The invention discloses a benzylation method for monosaccharide glucoside. The method includes the steps of sequentially adding monosaccharide glucoside, sodium hydride, methylbenzene and benzyl chloride to a reactor, raising the temperature to the reaction temperature of 60-130 DEG C, preserving heat till the reaction is completed, and conducting postprocessing on reaction liquid after the reaction ends to prepare a benzylation product of monosaccharide glucoside, wherein the benzylation product of monosaccharide glucoside is a product generated by conducting benzylation on all hydroxide radicals -OH on monosaccharide glucoside to generate -O-Bn, and Bn represents benzyl groups. Reaction solvent and extraction solvent are both methylbenzene, the postprocessing operation is simplified, the byproduct methylbenzene in the reaction process is consistent with the reaction solvent, recycled methylbenzene can be directly used as reaction solvent for the next batch without water removal, and the aims of simplifying operation, reducing sodium hydride and benzyl chloride unit consumption, effectively reducing generation of byproduct dibenzyl ether and reducing pollution are achieved.

Description

(1) Technical field [0001] The invention belongs to the field of chemistry, in particular to a method for benzylation of monosaccharide methyl glycoside. (2) Background technology [0002] The benzyl ether formed by the benzylation reaction of the sugar hydroxyl group is very stable to most acids and bases; it is also not affected by negative hydrogen reducing agents and mild oxidants, so it has a significant advantage in stability. The conditions for forming the protecting group are mild and the operation is simple. The benzylating reagents benzyl chloride and benzyl bromide are relatively cheap and easy to obtain. Pd / C-H 2 Hydrogenolysis is a characteristic deprotection reaction, and most protecting groups are compatible with it. Therefore, benzylation reaction is widely used in the synthesis of sugar derivatives. [0003] The commonly used benzylation method of monosaccharide methyl glycoside is the classic Williamson synthesis. First, the hydroxyl group and sodium h...

Claims

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Application Information

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IPC IPC(8): C07H15/18C07H1/00
Inventor 姜国平曹凌峰
Owner 浙江合糖科技有限公司
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