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Synthetic method of 5-hydroxymethyl furfural doped 2,3-unsaturated glucoside

A technology for the synthesis of hydroxymethylfurfural and a synthesis method, which is applied in the field of synthesis of 2,3-unsaturated glycosides, can solve the problems of low synthesis efficiency, catalyst use efficiency, catalyst inability to recycle, and inability to recycle, etc., to achieve low production cost, The effect of convenient operation and mild reaction conditions

Inactive Publication Date: 2016-11-16
EAST CHINA NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

(Filho, J.R.d.F.; Srivastava, R.M.; Soro, Y.; Cottier, L.; Descotes, G.J.Carbohydr.Chem.2001, 20, 561) but it also has the disadvantages of too long reaction time and the catalyst cannot be recycled.
[0004] Patent (CN201410039343.9) discloses a preparation method of 5-hydroxymethylfurfural, the method is to use FeCl in a suitable solvent 3 ·6H 2 O / C catalyst is prepared to obtain 5-hydroxymethylfurfural, and the product is separated and purified. However, the experimental method of Ferrier rearrangement reaction involving 5-hydroxymethylfurfural is time-consuming, the amount of acceptor is large, and it cannot be recycled. The synthesis efficiency is low. and catalyst efficiency are relatively low

Method used

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  • Synthetic method of 5-hydroxymethyl furfural doped 2,3-unsaturated glucoside

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] 216.8mg (0.80mmoL) of D-fructose and 2ml of dimethyl sulfoxide in 55mg of FeCl 3 ·6H 2 Under the catalysis of O / C (0.08mmoL) solid acid, the Ferrier rearrangement reaction was carried out, and the synthesized 5-hydroxymethylfurfural 101.3mg (0.80mmol) was directly used as the acceptor and donor in the next Ferrier rearrangement reaction without separation. After mixing 182.2mg (0.67mmol) of fully acetylated glucosene, add 7ml of dichloromethane and stir well, carry out Ferrier rearrangement reaction at room temperature, TLC (PE:EA=1:1) monitors the reaction is complete, and the catalyst is filtered out , dried and recovered for later use, the filtrate was concentrated and purified to obtain 185.3 mg of 2,3-unsaturated-4,6-di-O-acetylglucose 5'-furfuralmethanol glycoside, with a yield of 85%.

[0018] After nuclear magnetic spectrum detection and mass spectrometry analysis of the product obtained in Example 1, it can be determined that its structure is the target produc...

Embodiment 2

[0021] After mixing 99mg (0.77mmol) of 5-hydroxymethylfurfural with 81.6mg (0.63mmol) of fully acetylated glucosene, add 6ml of dichloromethane and stir thoroughly, and add 43mg of the first-time recycling in Example 1 at room temperature FeCl 3 ·6H 2 O / C solid acid catalyst (0.063mmoL) carries out Ferrier rearrangement reaction, TLC (PE:EA=1:1) monitoring reaction is complete, the catalyst is filtered out, dried and recovered for later use, and the filtrate is concentrated and purified to obtain the product as 2,3-unsaturated-4,6-di-O-acetylglucose 5'-furfural methanoside 160 mg, the yield was 76.5%.

Embodiment 3

[0023] After mixing 100mg (0.70mmol) of 5-hydroxymethylfurfural with 73.5mg (0.57mmol) of fully acetylated glucosene, add 5ml of dichloromethane and stir thoroughly, and add 37mg of the second recovery in Example 2 at room temperature FeCl 3 ·6H 2O / C solid acid catalyst (0.056mmoL) carries out Ferrier rearrangement reaction, TLC (PE:EA=1:1) monitoring reaction is complete, the catalyst is filtered out, dried and recovered for later use, and the filtrate is concentrated and purified to obtain the product as 2,3-unsaturated-4,6-di-O-acetylglucose 5'-furfural methanoside 126 mg, the yield was 66%.

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Abstract

The invention discloses a synthetic method of 5-hydroxymethyl furfural doped 2,3-unsaturated glucoside. The synthetic method is characterized in that a Ferrier rearrangement reaction is carried out on D-fructose in dimethyl sulfoxide by taking FeCl3 6H2O / C as a catalyst, prepared 5-hydroxymethyl furfural is not separated and is directly used as a receptor in the next Ferrier rearrangement reaction, and a one-pot reaction is carried out on the receptor and 2,3-unsaturated saccharides which are used as a donor to synthetize 2,3-unsaturated glucoside. Compared with the prior art, the synthetic method disclosed by the invention has the advantages that two reactions are used as the one-pot reaction to synthetize the 2,3-unsaturated glucoside, cyclic utilization of the catalyst is up to at least three times, the catalyst still has relative high catalytic activity, the technology is simple, the operation is convenient, the yield is high, the production cost is low, and the synthetic method is an environment-friendly, economical and efficient novel method for synthetizing the 2,3-unsaturated glucoside 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 synthesizing 2,3-unsaturated glycosides involving 5-hydroxymethylfurfural. Background technique [0002] 2,3-Unsaturated glycosides play an important role in carbohydrates and can be used to synthesize a series of important natural products, such as glycopeptides, nucleosides, etc. In addition, 2-deoxy sugars derived from 2,3 unsaturated glycosides can be used as effective chiral intermediates to synthesize biologically active compounds, such as coumarin nucleoside conjugates with obvious anti-hepatitis virus effects, etc. , and the Ferrier rearrangement reaction is an important method for the preparation of 2,3-unsaturated glycosides. 5-Hydroxymethylfurfural (HMF) is an important intermediate, which itself has certain biological activity and can also be used to synthesize a series of compounds with furan ring structure. These compo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H15/26C07H1/00
CPCC07H15/26C07H1/00
Inventor 张剑波马艺斌丁泽坤陈和善邱赛凤骆小胜
Owner EAST CHINA NORMAL UNIV
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