Method for preparing tribenoside

A technology of tribenzyl glucoside and tribenzyloxy group, which is applied in the field of preparation of tribenzyl glucoside, can solve the problems of low purity and long production cycle, and achieve the effect of good quality and high purity of the final product and avoid column chromatography operation

Active Publication Date: 2019-05-21
LUNAN BETTER PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] Aiming at the problems of long production cycle and low purity in the process of preparing tribenzyl glucoside at

Method used

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  • Method for preparing tribenoside
  • Method for preparing tribenoside
  • Method for preparing tribenoside

Examples

Experimental program
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Effect test

Embodiment 1

[0035] Synthesis of Intermediate I

[0036] At room temperature, add 8.40 kg of purified water into the three-necked bottle, slowly add 0.22 kg of concentrated sulfuric acid under stirring, and after stirring evenly, add 1.10 kg of acetic acid. When the temperature of the reaction solution rises to 65°C, add 1.10kg of 3,5,6-tribenzyloxy-1,2-oxo-isopropylidene-α-D-glucofuranose at one time, and then control the temperature at 65°C for reaction 10min. Under stirring, pour 2.60 kg of crushed ice into the reaction solution, add 10.60 L of dichloromethane, stir for 30 minutes, separate the organic phase; extract the water phase with 2.30 L of dichloromethane, combine the organic phases and wash with 10.60 × 2 kg of purified water; The dichloromethane phase was washed with a pre-prepared solution of 0.12kg sodium bicarbonate and 8.60kg purified water to pH=7~8; the dichloromethane phase was washed with 10.60kg purified water, and 3.00kg anhydrous sulfuric acid was added to the dich...

Embodiment 2

[0038] Synthesis of Intermediate I

[0039] At room temperature, add 8.40 kg of purified water into the three-necked bottle, slowly add 5.5 kg of concentrated sulfuric acid under stirring, and after stirring evenly, add 13.2 kg of acetic acid. When the temperature of the reaction solution rises to 100°C, add 1.10kg of 3,5,6-tribenzyloxy-1,2-oxo-isopropylidene-α-D-glucofuranose at one time, and then control the temperature at 100°C for reaction 120min. Under stirring, pour 2.60 kg of crushed ice into the reaction solution, add 10.60 L of dichloromethane, stir for 30 minutes, separate the organic phase; extract the water phase with 2.30 L of dichloromethane, combine the organic phases and wash with 10.60 × 2 kg of purified water; The dichloromethane phase was washed with a pre-prepared solution of 1.2kg sodium bicarbonate and 8.60kg purified water to pH=7~8; the dichloromethane phase was washed with 10.60kg purified water, and 3.00kg anhydrous sulfuric acid was added to the dic...

Embodiment 3

[0041] Synthesis of Intermediate I

[0042] At room temperature, add 8.40kg of purified water into the three-necked bottle, slowly add 0.22kg of concentrated sulfuric acid under stirring, and after stirring evenly, add 1.1kg of formic acid. When the temperature of the reaction solution rises to 65°C, add 1.10kg of 3,5,6-tribenzyloxy-1,2-oxo-isopropylidene-α-D-glucofuranose at one time, and then control the temperature at 65°C for reaction 10min. Under stirring, pour 2.60 kg of crushed ice into the reaction solution, add 10.60 L of dichloromethane, stir for 30 minutes, separate the organic phase; extract the water phase with 2.30 L of dichloromethane, combine the organic phases and wash with 10.60 × 2 kg of purified water; The dichloromethane phase was washed with a pre-prepared solution of 0.12kg sodium bicarbonate and 8.60kg purified water to pH=7~8; the dichloromethane phase was washed with 10.60kg purified water, and 3.00kg anhydrous sulfuric acid was added to the dichloro...

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Abstract

The invention belongs to the technical field, and concretely relates to a method for preparing tribenoside. The method comprises the specific steps: 3,5,6-tribenzyloxy-1,2-oxygen-isopropylidene-alpha-D-furanose is taken as a starting reactant, a deprotection reaction is carried out under acidic conditions to generate a 3,5,6-tribenzyloxy-D-glucofuranose crude product, two-time refining purification is carried out to obtain a 3,5,6-tribenzyloxy-D-glucofuranose pure product, and finally, ethyl-3,5,6-tribenzyloxy-D-glucopyranoside is obtained by etherification under acidic conditions. The methodof is used for preparing the tribenoside, and intermediate synthesis, separation and purification processes are simple and convenient, which avoid column chromatography operation, and the final product has good quality and high purity, and the production cycle can be shortened obviously.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry, and in particular relates to a preparation method of tribenzyl glycoside. Background technique [0002] Tribenoside (TBS), namely ethyl-3,5,6-tribenzyloxy-D-glucofuranoside, compound CAS registration number: 10310-32-4, the specific structural formula is as follows: [0003] [0004] Tribenzyl glycoside consists of two optical isomers, α and β. It is a capillary protective agent with anti-inflammatory, anti-toxin, healing wound tissue and weak analgesic effect, combined with sphingosine can preventively fight against Gram-negative and positive bacteria. 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 great...

Claims

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Application Information

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IPC IPC(8): C07H1/00C07H15/04
Inventor 张贵民王洪峰鲍广龙
Owner LUNAN BETTER PHARMA
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