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Synthetic method for 1,2-di-O-isopropylidene-3,5,6-tri-O-benzyl-D-glucofuranose

A technology of glucofuranose and isopropylidene, applied in 1, can solve the problems affecting the preparation of tribenzyl glucoside, lack of purity, low purity content, etc., and achieve the effect of less impurities, easy operation and high purity

Inactive Publication Date: 2016-10-26
山东康曼生物科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The impurities obtained by this method are more, and the purity content is lower, and the higher purity 1,2-di-O-isopropylidene-3,5,6-tri-O-benzyl-D-furan cannot be reached Glucose, affecting the preparation of tribenzyl glycoside in the next step

Method used

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  • Synthetic method for 1,2-di-O-isopropylidene-3,5,6-tri-O-benzyl-D-glucofuranose
  • Synthetic method for 1,2-di-O-isopropylidene-3,5,6-tri-O-benzyl-D-glucofuranose
  • Synthetic method for 1,2-di-O-isopropylidene-3,5,6-tri-O-benzyl-D-glucofuranose

Examples

Experimental program
Comparison scheme
Effect test

Embodiment example 1

[0036] Example 1: Preparation of 1,2-di-O-isopropylidene-3,5,6-tri-O-benzyl-D-glucofuran

[0037] Add 1,2-di-O-isopropylidene-D-glucofuranose (25g, 0.1135mol) into a 500ml three-necked flask containing benzyl chloride (150g, 1.185mol), heat it in an oil bath, and control the temperature Slowly add solid potassium hydroxide (76.3g, 1.362mol) under stirring at 85-95°C, the reaction is exothermic, control the adding speed so that the internal temperature does not exceed 95°C, and react for 3-4 hours. After the reaction is completed, cool the system down to 20-30°C, add water (100ml) dropwise, and then add n-hexane (100ml), stir for 15 minutes, let stand to separate the layers, and wash the organic layer with water (100ml), then wash at 40°C-45 Distill n-hexane under reduced pressure at ℃ until no flow out, sample HPLC detection, the results are as follows figure 2 shown. .

[0038] Purify the light yellow material after reduced evaporation by molecular distillation under spec...

Embodiment example 2

[0039] Example 2: Preparation of 1,2-di-O-isopropylidene-3,5,6-tri-O-benzyl-D-glucofuran

[0040] Add 1,2-di-O-isopropylidene-D-glucofuranose (25g, 0.1135mol) into a 500ml three-necked flask containing benzyl chloride (150g, 1.185mol), heat it in an oil bath, and control the temperature At 85-95°C, slowly add solid sodium hydroxide (56.8g, 1.419mol) under stirring, the reaction is exothermic, control the addition rate so that the internal temperature does not exceed 95°C, and react for 3-4 hours. After the reaction is completed, cool the system down to 20-30°C, add water (100ml) dropwise, and then add n-hexane (100ml), stir for 15 minutes, let stand to separate the layers, and wash the organic layer with water (100ml), then wash at 40°C-45 Distill n-hexane under reduced pressure at ℃ until no flow out, sample HPLC detection, the results are as follows Figure 4 shown.

[0041] Purify the light yellow material after reduced evaporation by molecular distillation under specific...

Embodiment example 3

[0042] Example 3: Preparation of 1,2-di-O-isopropylidene-3,5,6-tri-O-benzyl-D-glucofuran

[0043]Add 1,2-di-O-isopropylidene-D-glucofuranose (25g, 0.1135mol) into a 500ml three-necked flask containing benzyl chloride (180g, 1.422mol), heat it in an oil bath, and control the temperature Slowly add solid potassium hydroxide (79.5g, 1.419mol) under stirring at 90-100°C, the reaction is exothermic, control the addition rate so that the internal temperature does not exceed 100°C, and react for 3-4 hours. After the reaction is completed, cool the system down to 20-30°C, add water (100ml) dropwise, and then add n-hexane (100ml), stir for 15 minutes, let stand to separate the layers, and wash the organic layer with water (100ml), then wash at 40°C-45 Distill n-hexane under reduced pressure at ℃ until no flow out, sample HPLC detection, the results are as follows Figure 6 shown. .

[0044] Purify the light yellow material after reduced evaporation by molecular distillation under sp...

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Abstract

The invention discloses a synthetic method for a key tribenoside intermediate 1,2-di-O-isopropylidene-3,5,6-tri-O-benzyl-D-glucofuranose. The method comprises the following steps: adding 1,2-di-O-isopropylidene-D-glucofuranose as shown in a formula (I) which is described in the specification into benzyl chloride, controlling temperature, carrying out stirring and adding inorganic base; carrying out a nucleophilic substitution reaction under alkaline conditions; and then carrying out molecular distillation and purification so as to obtain high-purity high-content 1,2-di-O-isopropylidene-3,5,6-tri-O-benzyl-D-glucofuranose (II). The method provided by the invention has the advantages of mild reaction conditions, capacity of controlling generation of impurities, usage of a small amount of solvents, simple and convenient operation, no pollution and suitability for large-scale production; the manner of molecular distillation and purification can remove impurities which cannot be removed by using a common high temperature reduced-pressure distillation manner, product purity can reach 92.3%, and product content reaches 95%; and the high-content intermediate 1,2-di-O-isopropylidene-3,5,6-tri-O-benzyl-D-glucofuranose is beneficial for preparation of tribenoside (III).

Description

technical field [0001] The invention relates to a method for synthesizing and refining an important intermediate of tribenzyl glycoside, 1,2-di-O-isopropylidene-3,5,6-tri-O-benzyl-D-glucofuran. technical background [0002] Tribenoside (TBS), namely ethyl-3,5,6-tribenzyloxy-D-glucofuranoside, has anti-inflammatory, anti-toxin, enhances capillary tenacity, protects wound tissue and promotes its healing The role and weak analgesic effect, combined with sphingosine can preventive against Gram-negative and positive bacteria. [0003] The drug was discovered and synthesized in the 1950s, and was first developed by Japan in 1999 as an oral drug for the treatment of hemorrhoids. Because it is extremely fat-soluble, easily absorbed by the small intestine, and has a high drug utilization rate, its clinical efficacy is relatively high. Other similar drugs have greatly improved. [0004] Before the present invention, relevant data mentioned that the experimental method was as follows...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H9/04C07H1/00C07H1/06
CPCC07H1/00C07H1/06C07H9/04
Inventor 孙崇永胡自惠花卉孙继朋胡自豪
Owner 山东康曼生物科技有限公司
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