Synthesis method of salidroside

Abstract

The invention discloses a synthesis method of salidroside, which is implemented by taking p-hydroxyphenylethyl alcohol as a raw material through the steps of firstly, protecting hydroxyl by using methoxy-chloromethyl ether (MOMCl) or benzene sulfonyl chloride, benzoyl chloride and the like, and carrying out acylation and bromination on glucose so as to prepare tetra-acetyl-1-bromoglucose; then, reacting the protected p-hydroxyphenylethyl alcohol with the tetra-acetyl-1-bromoglucose in the presence of potassium superoxide or triethylamine and other organic alkalis, silver nitrate, silver carbonate and the like; and feeding hydrogen chloride gas into methanol so as to remove protecting groups on phenolic hydroxyl groups. According to the invention, by simplifying the synthesis process route, the reaction selectivity is improved, the production cost of salidroside is significantly reduced, and the increasing demands of people on salidroside are satisfied better.

Description

technical field

[0001] The invention relates to the technical field of chemical synthesis, in particular to a method for synthesizing salidroside. Background technique

[0002] With the increasing pace of human life and the increasing popularity of modern information means, fatigue and radiation have become serious problems that human beings generally face. Various rays and radioactive substances are ubiquitous in the environment of human life, and the radionuclides entering the body through diet and air cannot be ignored. Radiation can cause acute and chronic radiation injury, radiation mutagenesis and radiation carcinogenesis. The modern fast-paced life and work pressure can lead to long-term fatigue, which in turn leads to metabolic disorders of the body and various diseases. And fatigue can also increase the degree of radiation damage to the body. There are currently no effective solutions to these two types of problems.

[0003] At present, the radioprotectants at h...

Examples

Embodiment 1

[0030] (1) Synthesis of tetraacetylbromoglucose:

[0031]Mix anhydrous glucose, acetic anhydride and catalyst perchloric acid evenly at 0°C, raise the temperature to 30°C after half an hour, keep warm for 6 hours, then add red phosphorus, add bromine dropwise at 5°C, keep warm for half an hour, add water slowly, React at room temperature for 2 hours. After the reaction is completed, quickly extract the reaction solution with dichloromethane, combine the organic layers and wash twice with ice water, dry over anhydrous magnesium sulfate, and recover dichloromethane by distillation under reduced pressure to obtain a viscous solid. Add The viscous solid was dissolved in three times the amount of anhydrous ether, and left to stand overnight to obtain white needle-like crystals, which were filtered by suction and vacuum-dried to obtain the product tetraacetylglucosinobromide; the yield was 85%, and the purity was 95%.

[0032] (2) Hydroxyl protection of p-hydroxyphenylethanol:

[0...

Embodiment 2

[0045] (1) Synthesis of tetraacetylbromoglucose:

[0046] Mix anhydrous glucose, acetic anhydride and catalyst perchloric acid evenly at 10°C, raise the temperature to 50°C after half an hour, keep warm for 4 hours, then add red phosphorus, add bromine dropwise at 15°C, keep warm for half an hour, add water slowly, React at room temperature for 5 hours. After the reaction is completed, quickly extract the reaction solution with dichloromethane, combine the organic layers and wash twice with ice water, dry over anhydrous magnesium sulfate, and recover dichloromethane by distillation under reduced pressure to obtain a viscous solid. Add The viscous solid was dissolved in three times the amount of anhydrous ether, and stood overnight to obtain white needle-like crystals, which were filtered by suction and dried in vacuum to obtain the product tetraacetylglucosinobromide; the yield was 90%, and the purity was 96%.

[0047] (2) Hydroxyl protection of p-hydroxyphenylethanol:

[004...

Embodiment 3

[0060] (1) Synthesis of tetraacetylbromoglucose:

[0061] Mix anhydrous glucose, acetic anhydride and catalyst perchloric acid evenly at 5°C, raise the temperature to 35°C after half an hour, keep warm for 4.5h, then add red phosphorus, add bromine dropwise at 10°C, keep warm for half an hour, add water slowly , reacted at room temperature for 3.5 hours, after the reaction was completed, the reaction solution was extracted with dichloromethane quickly, the organic layers were combined and washed twice with ice water, dried over anhydrous magnesium sulfate, dichloromethane was recovered by distillation under reduced pressure to obtain a viscous solid, Three times the amount of anhydrous diethyl ether was added to the viscous solid to dissolve it, and it was allowed to stand overnight to obtain white needle-like crystals, which were filtered by suction and vacuum-dried to obtain the product tetraacetylglucosinobromide; the yield was 95%, and the purity was 97%.

[0062] (2) Hydr...

technical field

[0001] The invention relates to the technical field of chemical synthesis, in particular to a method for synthesizing salidroside. Background technique

[0002] With the increasing pace of human life and the increasing popularity of modern information means, fatigue and radiation have become serious problems that human beings generally face. Various rays and radioactive substances are ubiquitous in the environment of human life, and the radionuclides entering the body through diet and air cannot be ignored. Radiation can cause acute and chronic radiation injury, radiation mutagenesis and radiation carcinogenesis. The modern fast-paced life and work pressure can lead to long-term fatigue, which in turn leads to metabolic disorders of the body and various diseases. And fatigue can also increase the degree of radiation damage to the body. There are currently no effective solutions to these two types of problems.

[0003] At present, the radioprotectants at h...

Examples

Embodiment 1

[0030] (1) Synthesis of tetraacetylbromoglucose:

[0031]Mix anhydrous glucose, acetic anhydride and catalyst perchloric acid evenly at 0°C, raise the temperature to 30°C after half an hour, keep warm for 6 hours, then add red phosphorus, add bromine dropwise at 5°C, keep warm for half an hour, add water slowly, React at room temperature for 2 hours. After the reaction is completed, quickly extract the reaction solution with dichloromethane, combine the organic layers and wash twice with ice water, dry over anhydrous magnesium sulfate, and recover dichloromethane by distillation under reduced pressure to obtain a viscous solid. Add The viscous solid was dissolved in three times the amount of anhydrous ether, and left to stand overnight to obtain white needle-like crystals, which were filtered by suction and vacuum-dried to obtain the product tetraacetylglucosinobromide; the yield was 85%, and the purity was 95%.

[0032] (2) Hydroxyl protection of p-hydroxyphenylethanol:

[0...

Embodiment 2

[0045] (1) Synthesis of tetraacetylbromoglucose:

[0046] Mix anhydrous glucose, acetic anhydride and catalyst perchloric acid evenly at 10°C, raise the temperature to 50°C after half an hour, keep warm for 4 hours, then add red phosphorus, add bromine dropwise at 15°C, keep warm for half an hour, add water slowly, React at room temperature for 5 hours. After the reaction is completed, quickly extract the reaction solution with dichloromethane, combine the organic layers and wash twice with ice water, dry over anhydrous magnesium sulfate, and recover dichloromethane by distillation under reduced pressure to obtain a viscous solid. Add The viscous solid was dissolved in three times the amount of anhydrous ether, and stood overnight to obtain white needle-like crystals, which were filtered by suction and dried in vacuum to obtain the product tetraacetylglucosinobromide; the yield was 90%, and the purity was 96%.

[0047] (2) Hydroxyl protection of p-hydroxyphenylethanol:

[004...

Embodiment 3

[0060] (1) Synthesis of tetraacetylbromoglucose:

[0061] Mix anhydrous glucose, acetic anhydride and catalyst perchloric acid evenly at 5°C, raise the temperature to 35°C after half an hour, keep warm for 4.5h, then add red phosphorus, add bromine dropwise at 10°C, keep warm for half an hour, add water slowly , reacted at room temperature for 3.5 hours, after the reaction was completed, the reaction solution was extracted with dichloromethane quickly, the organic layers were combined and washed twice with ice water, dried over anhydrous magnesium sulfate, dichloromethane was recovered by distillation under reduced pressure to obtain a viscous solid, Three times the amount of anhydrous diethyl ether was added to the viscous solid to dissolve it, and it was allowed to stand overnight to obtain white needle-like crystals, which were filtered by suction and vacuum-dried to obtain the product tetraacetylglucosinobromide; the yield was 95%, and the purity was 97%.

[0062] (2) Hydr...