CN105646610A - Chemical synthesis process for preparing gastrodin and similar phenolic glucoside thereof - Google Patents

Abstract

The present invention discloses a chemical synthesis process for preparing gastrodin and similar phenolic glucoside represented by a formula (I) thereof. According to the present invention, industrial easily-available raw materials such as acetic anhydride and acetyl bromide or PHOSPHORUS TRIBROMIde or phosphorus pentabromide are used to complete the hydroxy protection of glycosyl and the bromination reaction of hemiacetal hydroxy, such that the problems that the use of red phosphorus and bromine during the gastrodin bulk drug production process causes physical and psychological harm on production workers and environment pollution and damage are solved; and the process mainly comprises two steps of key reactions, wherein the first step reaction is synthesis of bromoacetyl glycosyl compound, and the second step reaction is condensation of the bromoacetyl glycosyl compound and a phenolic compound to generate the acetyl-protected phenolic glucoside compound.

Description

Prepare the chemical synthesis process of Gastrodine and analogous henolic glycoside formula thereof

Technical field

The invention belongs to medicine synthesis technical field, it is specifically related to a kind of chemical synthesis process preparing Gastrodine and analogous henolic glycoside formula thereof.

Background technology

The chemical synthesis process preparing Gastrodine and analogous henolic glycoside formula thereof at least comprises the processes such as drying, condensation reaction, hydrolysis reaction. In current Gastrodine and analogous henolic glycoside formula building-up process method thereof, technical process is not easy to implement, the Gastrodine and the analogous henolic glycoside formula finished product purity thereof that generate are low, reaction residual cannot be recycled, production process is complicated, production efficiency is low and cost height, is not suitable for scale operation.

Summary of the invention

In order to overcome the above-mentioned technical problem that prior art exists, it is an object of the invention to, a kind of chemical synthesis process preparing Gastrodine and analogous henolic glycoside formula thereof is provided, the present invention not only production process simple, increase work efficiency, and the Gastrodine generated and analogous henolic glycoside formula product purity thereof are big, it is applicable to suitability for industrialized production.

The chemical synthesis process preparing Gastrodine and analogous henolic glycoside formula thereof provided by the invention, comprises the following steps:

(1) taking diacetyl oxide and acetyl bromide or phosphorus tribromide or phosphorus pentabromide as reagent, by the reaction with sugar base, both having protected the hydroxyl in sugar base, meanwhile, bromine, for hemiacetal hydroxyl, obtains bromoacetyl glycosyl compound;

(2) in acetone and water reaction system, add the iodide ion of catalytic amount, taking sodium hydroxide or potassium hydroxide as alkali reagent, bromoacetyl glycosyl compound and phenoloid react in the ratio of 3: 1��1: 3, TLC detection reaction process, after reaction terminates, obtain the phenolic glycosides compound of ethanoyl protection;

(3) in sodium methylate and methyl alcohol or sodium ethylate and ethanolic soln, slough acetyl protection base, obtain final product phenolic glycosides compound.

The chemical synthesis process preparing Gastrodine and analogous henolic glycoside formula thereof provided by the invention, its useful effect is, overcoming prior art, to prepare operation in Gastrodine and analogous henolic glycoside formula technological process thereof more, the problem that workload is big, it is to increase working efficiency; Improve the per pass conversion of reactant and the product rate of resultant.

Embodiment

Below in conjunction with an embodiment, the chemical synthesis process preparing Gastrodine and analogous henolic glycoside formula (I) thereof provided by the invention is described in detail.

Embodiment

The chemical synthesis process preparing Gastrodine and analogous henolic glycoside formula thereof of the present embodiment, comprises the following steps:

(1) taking diacetyl oxide and acetyl bromide or phosphorus tribromide or phosphorus pentabromide as reagent, by the reaction with sugar base, both having protected the hydroxyl in sugar base, meanwhile, bromine, for hemiacetal hydroxyl, obtains bromoacetyl glycosyl compound;

(2) in acetone and water reaction system, add the iodide ion of catalytic amount, taking sodium hydroxide or potassium hydroxide as alkali reagent, bromoacetyl glycosyl compound and phenoloid react in the ratio of 3: 1, TLC detection reaction process, after reaction terminates, obtain the phenolic glycosides compound of ethanoyl protection;

(3) in sodium methylate and methyl alcohol or sodium ethylate and ethanolic soln, slough acetyl protection base, obtain final product phenolic glycosides compound.

Prepare the chemical synthesis process of Gastrodine and analogous henolic glycoside formula thereof, it is not necessary to loaded down with trivial details post-reaction treatment, substantially increases product performance, and it is environmentally friendly pollution-free, technical process is easy to implement, and production cost is low, synthesis output height, better achieves the suitability for industrialized production of product.

Claims (1)

1. prepare Gastrodine and the chemical synthesis process of analogous henolic glycoside formula (I) thereof for one kind, it is characterised in that: described method comprises the following steps:

(1) taking diacetyl oxide and acetyl bromide or phosphorus tribromide or phosphorus pentabromide as reagent, by the reaction with sugar base, both having protected the hydroxyl in sugar base, meanwhile, bromine, for hemiacetal hydroxyl, obtains bromoacetyl glycosyl compound;

(2) in acetone and water reaction system, add the iodide ion of catalytic amount, taking sodium hydroxide or potassium hydroxide as alkali reagent, bromoacetyl glycosyl compound and phenoloid react in the ratio of 3: 1��1: 3, TLC detection reaction process, after reaction terminates, obtain the phenolic glycosides compound of ethanoyl protection;

(3) in sodium methylate and methyl alcohol or sodium ethylate and ethanolic soln, slough acetyl protection base, obtain final product phenolic glycosides compound.