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A kind of preparation method of tribenzyl glycoside

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

Active Publication Date: 2022-02-08
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 present, a new method of purifying intermediate I by two-step refining method to obtain the target compound is provided

Method used

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  • A kind of preparation method of tribenzyl glycoside
  • A kind of preparation method of tribenzyl glycoside
  • A kind of preparation method of tribenzyl glycoside

Examples

Experimental program
Comparison scheme
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 of medicine, and in particular relates to a preparation method of tribenzyl glycoside. The specific steps include: using 3,5,6-tribenzyloxy-1,2-oxygen-isopropylidene-α-D-glucofuran as the starting reactant, deprotection reaction occurs under acidic conditions to generate 3, The crude product of 5,6-tribenzyloxy-D-glucofuran was refined and purified twice in turn to obtain the pure product of 3,5,6-tribenzyloxy-D-glucofuran, which was finally prepared by etherification under acidic conditions. Get ethyl-3,5,6-tribenzyloxy-D-glucofuranoside. The method of the invention prepares tribenzyl glucoside, the intermediate synthesis and separation and purification are simple and convenient, avoids column chromatography operation, and the final product has good quality and high purity, and the production cycle can be obviously shortened.

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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Patent Type & Authority Patents(China)
IPC IPC(8): C07H1/00C07H15/04
Inventor 张贵民王洪锋鲍广龙
Owner LUNAN BETTER PHARMA
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