Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

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
View PDF7 Cites 4 Cited by
  • 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 point, which limits the selectable temperature range of the benzylation reaction; or the solvent itself is unstable under alkaline conditions ; or the used solvent has a narrow range of application, and can only synthesize all-benzyl products, and it is difficult to recover, has high toxicity, consumes raw material sodium hydrogen, and increases by-product toluene

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Benzylation method for monosaccharide glucoside
  • Benzylation method for monosaccharide glucoside
  • Benzylation method for monosaccharide glucoside

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

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

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

Embodiment 2

[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 tube, add methyl-α-D-glucopyranoside 9.7g (50.0mmol) 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, tracked by liquid chromatography, and kept warm until the reaction was complete. After the heat preservation reaction is completed, cool down to about 60°C, slowly add water dropwise, and react with the residual sodium hydride until no bubbles are formed. The solid matter was removed by filtration, and the filter cake was washed with 15 ml x 2 times of toluene, and the organic layers were combined. The organic layer was heated to 65-70° C., washed with water until neutral, and washed with 20 ml of water each time, and washed 3-4 times (the first washing water was discarded, and the other washin...

Embodiment 3

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

[0047] In a 250ml three-neck flask equipped with a stirrer, a thermometer, and a reflux separator (equipped with a condenser tube), 10.6g (50.0mmol) of methyl-α-D-galactopyranoside monohydrate, toluene 100ml, heat up to 90-95°C, control the vacuum degree -0.03--0.04Mpa, reflux and divide water to remove the crystal water in methyl-α-D-galactopyranoside monohydrate. After dehydration is completed, cool down to 35-40°C, and change the reflux water separator to a reflux condensing device. Add sodium hydride paraffin oil dispersion (content 55%) 10.0g (229.2mmol) and benzyl chloride 30.5g (240.9mmol) successively, heat up to about 90-95°C, follow by liquid chromatography, 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 the residual sodium hydride until no bubbles are formed. The solid matter was removed by fi...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07H15/18C07H1/00
Inventor 姜国平曹凌峰
Owner 浙江合糖科技有限公司
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com