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A kind of synthesis method of acetylated δ-hydroxyl-α, β-unsaturated furfural

A synthesis method and acetylation technology, applied in chemical instruments and methods, esterification saccharide, organic chemistry, etc., can solve the problems of harsh reaction conditions, high production cost, high price, etc., and achieve mild reaction conditions and non-toxic price. , the effect of convenient operation

Active Publication Date: 2021-03-26
EAST CHINA NORMAL UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

(Saquib, M.; Sagar, R.; Shaw, A.K.Carbohydr.Res.2006,341,1052) Although this method avoids highly toxic mercury sulfate, the reaction temperature is very high, and it requires two expensive metal catalysts to act together to get the target product
In 2011, Ramesh used InCl 3 As a catalyst, Perlin aldehyde after ring-opening of acetylated glucose and acetylated galactose was synthesized. The obtained Perlin aldehyde is a mixture of two compounds containing 4-position hydroxyl or 5-position hydroxyl. After acylation of the hydroxyl group, the total yield is 60 % to obtain the target product (Nagaraj, P.; Ganesan, M.; Ramesh, N.G.Tetrahedron 2011,67,769) but the reaction time will be 5-7h, the scope of application is limited, and expensive and poisonous InCl is used as catalyst
[0004] In summary, the Perlin aldehyde synthesis process of the prior art is complicated, the reaction conditions are harsh, the yield is low, the raw material consumption is large and toxic, and the production cost is high, which seriously restricts the wide application of this type of molecule

Method used

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  • A kind of synthesis method of acetylated δ-hydroxyl-α, β-unsaturated furfural

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Experimental program
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Effect test

Embodiment 1

[0017] Add 40.8mg (0.15mmol) of peracetylated glucosene, 20mL of acetone and 1mL of water into the flask, stir in an oil bath at 50°C, and then add 24.2mg (0.090mmol) of FeCl 3 ·6H 2 O catalyst, TLC monitors the reaction until the raw material is reacted, the reaction solution is cooled to room temperature, and water is added to quench the reaction, after being extracted with DCM, the organic phase is combined, and after being washed with saturated NaCl solution, it is dried and concentrated to obtain Perlin aldehyde, which is used in the ring-opening reaction Add 5 mL of DCM to the product, then add 31.4 μl triethylamine, 1.8 mg DMAP and 19 μl acetic anhydride in sequence, carry out acetylation reaction at 35 ° C, monitor the reaction by TLC until the reaction of the raw materials is complete, add saturated NH 4 The reaction was quenched with Cl solution, extracted with DCM, dried, and column chromatographed to obtain a pure product of 35.5 mg of Perlin glucuronide with an ac...

Embodiment 2

[0022] Add 32.1 mg (0.15 mmol) of fully acetylated rhamnose, 30 mL of dichloromethane and 1 mL of water into the flask, stir in an oil bath at a temperature of 25 ° C, and then add 2.5 mg (0.015 mmol) of FeCl 3 Catalyst, TLC monitors the reaction, until the raw material has reacted, after the reaction solution is cooled to room temperature, water is added to quench the reaction, after being extracted with DCM, the organic phase is combined, washed with saturated NaCl solution, dried and concentrated to obtain Perlin aldehyde, which is used in the ring-opening reaction Add 5mL DCM to the product, then add 25μl triethylamine, 5mg DMAP and 17μl acetic anhydride in sequence, carry out acetylation reaction at 0°C, monitor the reaction by TLC until the reaction of the raw materials is complete, add saturated NH 4 The reaction was quenched with Cl solution, extracted with DCM, dried, and column chromatographed to obtain 19.8 mg of Perlin rhamnoaldehyde with acetylated protecting group...

Embodiment 3

[0027] Add 30.0mg (0.15mmol) fully acetylated arabinose, 30mL acetonitrile and 0.5mL water into the flask, stir in an oil bath at 80°C, then add 15.1mg (0.09mmol) FeCl 3 Catalyst, TLC monitors the reaction, until the raw material has reacted, after the reaction solution is cooled to room temperature, water is added to quench the reaction, after being extracted with DCM, the organic phase is combined, washed with saturated NaCl solution, dried and concentrated to obtain Perlin aldehyde, which is used in the ring-opening reaction Add 5mL DCM to the product, then add 35μl triethylamine, 3mg DMAP and 19μl acetic anhydride in sequence, carry out acetylation reaction at 15°C, monitor the reaction by TLC until the reaction of the raw materials is complete, add saturated NH 4 The reaction was quenched with Cl solution, extracted with DCM, dried, and column chromatographed to obtain 26.4 mg of Perlin arabinfural, an acetylated protecting group, with a yield of 88%.

[0028] The product...

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Abstract

A synthetic method of acetylated delta-hydroxy-alpha,beta-unsaturated furfural is disclosed. The method is characterized in that a glucal having a protective group, an organic solvent and water are mixed according to mole-volume ratio of 1 mol:50-250 L:0.6-2.8 L, a ring-opening reaction is performed by adopting FeCl3 as a catalyst, a product is mixed with triethylamine, DMAP and acetic anhydride according to a molar ratio of 1:1-3:0.1-0.5:0.5-3.0, the mixture is subjected to acetaylation at 0-45 DEG C, and neutralization, extraction and purification are performed after the reaction is finishedto obtain acetylated delta-hydroxy-alpha,beta-unsaturated furfural having different protective groups. Compared with the prior art, the method has characteristics of a simple process, convenient operation, nontoxic and economical agents, mild reaction conditions and a high reaction speed and a high yield, and is a green, economical and efficient novel acetylated Perlin aldehyde synthetic method having a good application prospect.

Description

technical field [0001] The invention relates to the technical field of organic synthesis intermediates, in particular to a method for synthesizing acetylated δ-hydroxyl-α, β-unsaturated furfural. Background technique [0002] Due to the fact that sugar molecules contain multiple hydroxyl groups and multiple inherent chiral centers, as well as the widespread occurrence of sugars in nature, sugar molecules and their derivatives are widely used in the synthesis of natural products and many important biological activities. More and more chemists pay attention to the application of compounds, sugar molecules and their derivatives in synthesis. Perlin aldehyde, also known as δ-hydroxy-α, β-unsaturated furfural, is a very important class of organic intermediates. This type of molecule contains multiple functional groups such as hydroxyl, aldehyde and conjugated double bonds, which can be used for related Hydroxyl-related reactions, such as the protection and deprotection of the hy...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H13/06C07H1/00
CPCC07H1/00C07H13/06Y02P20/55
Inventor 张剑波陈和善郭红丁泽坤
Owner EAST CHINA NORMAL UNIV
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