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Selective modification method of cane sugar primary hydroxyl

A modification method and primary hydroxyl technology, applied in the field of chemistry, can solve the problems of easy hydrolysis and cleavage, large steric hindrance, limited chemical modification, etc., and achieve the effects of not easy sucrose glycosidic bond cleavage, mild reaction conditions, and high product yield.

Inactive Publication Date: 2015-07-01
SHENZHEN INST OF ADVANCED TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] (1) Sucrose has three primary hydroxyl groups (6, 6′, 1′ hydroxyl groups). Due to the large steric hindrance of the 1′ hydroxyl group, the activity is the lowest, while the activity between the 6′ hydroxyl group and the 6′ hydroxyl group The difference is small, and selective modification is difficult to achieve; (2) sucrose glycosidic bonds are easily hydrolyzed and broken under acidic conditions. Studies have shown that 0.1% methanolic hydrochloric acid solution can completely hydrolyze sucrose within 30 minutes, and sucrose is particularly acid-sensitive. The nature greatly limits the chemical modification of the primary hydroxyl groups of sucrose, and so far there is no effective method for the selective modification of the primary hydroxyl groups of sucrose

Method used

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  • Selective modification method of cane sugar primary hydroxyl
  • Selective modification method of cane sugar primary hydroxyl
  • Selective modification method of cane sugar primary hydroxyl

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] (1) After dissolving sucrose in anhydrous N,N-dimethylformamide (DMF), slowly add sodium hydride whose molar mass is 9.6 times the molar mass of sucrose, and stir at room temperature for 30 minutes, then slowly dropwise add a molar mass of Benzyl bromide with 9.6 times the molar amount of sucrose was reacted at room temperature for 24 hours. After the reaction was monitored, the reaction solution was obtained. After the reaction was quenched by slowly adding methanol dropwise to the reaction solution under an ice bath, the excess bromide was reacted for another 2 hours. Benzyl was reacted, DMF was distilled off under reduced pressure to obtain a residue, the residue was dissolved in ethyl acetate, and the insoluble matter was filtered out with a short silica gel column to obtain a filtrate. Sucrose, the yield of octabenzyl sucrose is 75%, and the reaction equation is:

[0057]

[0058] The NMR data of the product are:

[0059] 1 H NMR (400 MHz, deuterated chlorofor...

Embodiment 2

[0069] Step (1) of this embodiment is the same as step (1) of Embodiment 1;

[0070](2) Dissolve octabenzyl sucrose in anhydrous benzene to obtain an octabenzyl sucrose solution with a concentration of 1mol / L. After removing the air, add the octabenzyl sucrose solution to the mixture of dicobalt octacarbonyl and triethylsilane In the solution, stir and react under reflux for 18 hours to remove the 6,6'-position dibenzyl group. The molar weight of dicobalt octacarbonyl is three times that of octabenzyl sucrose, and the molar weight of triethylsilane is octabenzyl 10 times the molar weight of sucrose. After monitoring the reaction, the reaction solution was obtained, and an appropriate amount of pyridine was added, then bubbled with air for 20 minutes, and the reaction solution was filtered through a silica gel column to obtain the filtrate. The filtrate was washed with ethyl acetate and then combined and concentrated. Chromatographic separation yielded sucrose whose 6,6′-hydrox...

Embodiment 3

[0078] Steps (1) (2) of this embodiment are the same as steps (1) (2) of Embodiment 1;

[0079] (3) Dissolve sucrose whose 6′-hydroxyl group is protected by triethylsilyl group in tetrahydrofuran, then add TBAF whose molar mass is 1.2 times the molar amount of sucrose whose 6′-position hydroxyl group is protected by triethylsilyl group, and react at room temperature After 30 minutes, the triethylsilyl group was removed. After monitoring the end of the reaction, the reaction solution was directly evaporated to dryness to obtain a residue. The residue was dissolved in ethyl acetate and filtered through a silica gel column to obtain the filtrate. The filtrate was evaporated to dryness to obtain the free Sucrose, dissolve the free sucrose at the 6′ hydroxyl group in an appropriate amount of pyridine, add an appropriate amount of acetic anhydride, and after about 3 hours of esterification, the molar amount of acetic anhydride is 5 times that of the free sucrose at the 6′ hydroxyl gr...

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Abstract

The invention provides a selective modification method of cane sugar primary hydroxyl. The selective modification method comprises the following steps: firstly, performing full-benzylation on cane sugar, by taking the full-benzylated cane sugar as a substrate, adding dicobalt octacarbonyl and silane, and performing selective removal on primary hydroxyl; substituting primary hydroxyl by using triethyl-silyl so as to obtain cane sugar of which 6'-hydroxyl is protected by triethyl-silyl or cane sugar of which 6,6'-hydroxyl is protected by triethyl-silyl, further removing triethyl-silyl by using tetrabutyl ammonium fluoride so as to obtain cane sugar of which 6'-hydroxyl is free or cane sugar of which 6,6'-hydroxyl is free. Selective modification and successive modification on 6,6'-primary hydroxyl can be achieved, and the selective modification method is good in selectivity, gentle in reaction condition and high in product yield.

Description

technical field [0001] The invention belongs to the technical field of chemistry, and in particular relates to a method for selectively modifying primary hydroxyl groups of sucrose. Background technique [0002] Sucrose is the most easily obtained low-molecular-weight oligosaccharide in nature, and its chemical structure is As an organic raw material, its price is low, its purity is high, and its properties are stable, so it is widely favored by the industry; the terminal modification of sucrose (ie, the chemical modification of primary hydroxyl groups) is the most important research direction of sucrose chemistry, but due to the complex structure However, its terminal modification faces the following two difficulties: [0003] (1) Sucrose has three primary hydroxyl groups (6, 6′, 1′ hydroxyl groups). Due to the large steric hindrance of the 1′ hydroxyl group, the activity is the lowest, while the activity between the 6′ hydroxyl group and the 6′ hydroxyl group The differ...

Claims

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Application Information

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IPC IPC(8): C07H23/00C07H1/00
Inventor 赵岳涛王怀雨潘浩波李中军
Owner SHENZHEN INST OF ADVANCED TECH
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