The invention discloses a separation method suitable for chemical synthesis of salidroside for industrial production. The method comprises the following steps: carrying out a reaction on Beta-D-pent-acetyl glucose and hydroxyphenethyl alcohol under the catalytic action of a lewis acid; and carrying out deacetylation on a generated tetraacetyl salidroside product so as to prepare the salidroside. Thus, the salidroside product is synthesized in a separating manner via an extraction and recrystallization method while a simple and convenient synthesis method is adopted at the same time. Compared with the traditional chemical synthesis process, the method disclosed by the invention is low in cost, high in yield, short in reaction time, simple and simple, convenient and environmentally friendly in synthesis process, thereby being suitable for industrial production, and the raw materials are easily available.

Separation method suitable for chemical synthesis of salidroside for industrial production

The invention discloses a method for catalytic synthesis of salidroside. The method comprises the following steps: enabling total acetyl glucose to react with 4-benzyloxy-phenethyl alcohol under the action of a catalyst to obtain 2-(4-benzyloxyphenyl)ethyl-(2,3,4,6-O-tetra-acetyl)-beta-D-glucopyranoside, wherein the catalyst is tin chloride, zinc oxide, aluminum trichloride, boron fluoride or copper chloride, or a mixture of one of tin chloride, zinc oxide, aluminum trichloride, boron fluoride and copper chloride as well as magnesium fluoride, magnesium chloride, magnesium bromide or magnesium iodide; and removing an acetyl protective group from the product in the presence of an organic base to obtain 2-(4-benzyloxyphenyl)ethyl-beta-D-glucopyranoside, and introducing hydrogen into 2-(4-benzyloxyphenyl)ethyl-beta-D-glucopyranoside under the catalysis of palladium and carbon to perform reduction reaction so as to remove a benzyl protective group, thereby obtaining 2-(4-hydroxyphenyl)ethyl-beta-D-glucopyranoside. The method disclosed by the invention has the outstanding characteristics that the yield is high, the total acetyl glucose is subjected to three steps of reaction, the total yield can reach 63%, the process is simple, the cost is low, and the method is suitable for industrial mass production.

Method for catalytic synthesis of salidroside

The invention relates to the field of sugar compounds and in particular relates to a method for preparing 2,3,4,6-tetra-O-benzyl -D-galactose. The method comprises the steps of preparing benzothiazolylthioacetyl galactose from galactose in the presence of acetic anhydride, catalysts and 2-mercaptobenzothiazole, preparing benzothiazolylthiotetrabenzyl galactose from benzothiazolylthioacetyl galactose in the presence of potassium hydroxide and benzyl chloride, and preparing 2,3,4,6-tetra-O-benzyl -D-galactose from benzothiazolylthiotetrabenzyl galactose in the presence of N-bromosuccinimide. The method has the beneficial effects that 2,3,4,6-tetra-O-benzyl -D-galactose is synthesized by a three-step reaction method, so that the purity and yield of the product are effectively increased; the method is simple to operate; the raw materials are accessible; the operating cost and the materials are saved.

Method for preparing 2,3,4,6-tetra-O-benzyl -D-galactose

The invention discloses a synthesis method for salidroside and an intermediate compound obtained in the synthesis method. The synthesis method comprises the following steps: (1) under the catalytic action of Lewis acid, carrying out a reaction between hydroxyl-protected benzyl carbinol and acyl-protected glucose ester to obtain the intermediate compound shown in formula (IV); (2) putting the intermediate compound shown in formula (IV) in C1-C4 alkanol, removing acyl protecting groups in the presence of alkali, and carrying out drying to obtain salidroside shown in the formula (I). The detailed definitions of substituent groups in formula (III) and formula (IV) are shown in the description. The synthesis method has the advantages of being simple to operate, mild in condition, high in yield and easy for industrialization.

Synthesis method for salidroside and intermediate compound obtained in synthesis method

The invention discloses a chemical synthesis method of lupeose. The method comprises the following steps: by taking full benzyl galactose thioglycoside as a glycosyl donor, converting a saccharose receptor into raffinose, selectively removing the remote primary benzyl of the raffinose to obtain the saccharose receptor-hydroxyl free raffinose needed by the next glycosylation, taking the full benzyl galactose thioglycoside as a donor to obtain all-protected lupeose, removing the protecting group in the all-protected lupeose to obtain the lupeose. The invention aims to establish a chemical synthesis method of the lupeose with simple and convenient process, high yield and mild condition.

Chemical synthesis method of lupeose

The invention discloses a method for chemically synthesizing natural product salidroside In the method, lewis acid serving as a catalyst, tyrosol of acyl protected phenolic hydroxyl serving as a glycosylation receptor, and beta-D-5 acetyl glucose serving as glycosylation donor perform a glycosylation reaction to obtain 1-[2-(4-acyloxy phenyl) ethyl]-2,3,4,6-O-tetraacetyl-beta-D-glucopyranoside; and acyl protecting group is removed in an alkaline condition to obtain salidroside Compared with the traditional method, the method has easily available raw materials, the glycosylation receptor, the glycosylation product and the final product can be prepared through recrystallization, column chromatography and other purification processes are eliminated, the reaction step is short, the preparation process is simple, the glycosylation reaction catalyst has low cost and is easily available, so that the preparation cost is remarkably reduced; and a heavy metal salt catalyst is not used in the reaction, so that the synthesis product is more suitable to be used as a raw material of medicaments and health-care products The method is suitable for industrial production of salidroside

Salidroside chemical synthesis method for industrialization

The invention discloses a novel method for regioselectively removing O-benzyl protective group of sugar. The reaction conditions are mild and the selectivity is high. Moreover, the invention additionally provides formula (IV) intermediate compound. Definitions of substituent groups are detailed in an instruction book.

Method for regioselectively removing O-benzyl protective group of sugar

The invention discloses a method for synthesis of chondroitin sulfate tetrasaccharide. The method comprises that orderly through enzymatic hydrolysis, protecting group protection, protecting group conversion, selective deprotection, hydroxyl oxidation and selective reduction, an intermediate compound shown in the formula O is prepared from hyaluronate as a starting material, and chondroitin sulfate tetrasaccharide is prepared from the intermediate compound shown in the formula O, wherein substituents in the formula O are specifically defined in the specification. The invention provides the intermediate compound for synthesis of chondroitin sulfate tetrasaccharide. Compared with the existing synthesis method, the method provided by the invention has the advantages of simple synthesis route, no glycosylation reaction, high reaction yield and good application prospect.

Method for synthesis of chondroitin sulfate tetrasaccharide and intermediate compound

The invention discloses a fucosylated chondroitin sulfate oligosaccharide glycocluster with a structure show in general formula Q in the description Definitions of substituent groups are detailed inthe description The glycocluster compound is synthesized from chondroitin sulfate A salt as a raw material by acidolysis, protecting group operation and glycosylation in sequence on the basis of molecules of multifunctional groups as molecular skeletons The glycocluster can simulate activity of natural glycosaminoglycan based on glycocluster effect, and can be applied to the medical field due tostructural certainty

Fucosylated chondroitin sulfate oligosaccharide glycocluster and preparation method thereof

The invention discloses a hyaluronic acid oligosaccharides sugar cluster compound shown as a formula I , and the definition of the groups in the formula I is shown as a specification. In addition, the invention also discloses a preparation method and a purpose of the compound. The sugar cluster based on hyaluronic acid oligosaccharides in the formula I has similar capability for combining CD44 with high molecular weight hyaluronic acid, and overcomes the disadvantages of high viscoelasticity and poor druggability of the high molecular weight hyaluronic acid.

Sugar cluster compound and its pharmaceutically acceptable salt, purpose thereof and pharmaceutical composition

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