Synthetic method for cordycepin

Abstract

The invention discloses a synthetic method for cordycepin. The method comprises the following steps: with adenosine as a starting material, subjecting adenosine and Mattock's bromide to bromination in a reaction solvent of acetonitrile and/or ethyl acetate during implementation of hydroxyl protection so as to obtain two products, i.e., 5'-[2,5,5-trimethyl-1,3-dioxolane-4-one-2-yl]-3'-bromo-3'-deoxy-2'-O-acetyl adenosine and 5'-[2,5,5-trimethyl-1,3-dioxolane-4-one-2-yl]-2'-bromo-2'-deoxy-3'-O-acetyl adenosine; then removing protective groups so as to obtain 3'-bromo-3'-deoxy-adenosine hydrochloride; and subjecting 3'-bromo-3'-deoxy-adenosine hydrochloride to debromination so as to obtain 3'-deoxyadenosine, i.e., cordycepin. The synthetic method provided by the invention is simple to operate, has short reaction steps and does not need purification in the process of reaction; and the purity and each index of the obtained cordycepin product are better than a currently commercially available cordycepin product.

Description

technical field [0001] The invention relates to a synthesis method, in particular to a synthesis method of cordycepin. Background technique [0002] Cordycepin, namely 3'-deoxyadenosine (3'-deoxyadenosine, 3'-dA) is a nitrogen glycoside nucleic acid derivative and belongs to the purine alkaloids. Its molecular formula is C 10 h 13 N 5 o 3 , the relative molecular weight is 251, the melting point is 230-231 ℃, soluble in water, hot ethanol and methanol, insoluble in benzene, ether and chloroform, the maximum external absorption is 259nm. Cordycepin was discovered by German scientists Cunningham et al. in 1951, and Kaczka et al. gave the exact structure of the compound in 1964. Since then, research on the pharmacological action, biological activity, extraction, biosynthesis and chemical synthesis of this compound has become more and more active. According to reports by Cai Youhua et al., cordycepin mainly has the following pharmacological effects: inhibition of microbial...

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Problems solved by technology

[0003] In literature (Tetrahedron Letters, 2004, vol.45, #1p.137-140), the report on the preparation method of cordycepin, the problem of this method is that the process steps are long, the yield is low, and lithium triethylborohydride is used , prone to spontaneous combustion and certain toxicity

The defect of this method is exactly strong dependence on resources, time-consuming, labor-intensive, and expensive to produce, and it is more troublesome to obtain a product with high purity (more than 99%), and it is difficult to produce on a large scale; 2. Biological fermentation: prepare and separate by biological fermentation Purification technology

Compared with plant extraction, this method has great advantages, but there is no fundamental improvement. The workload of its separation and purification is large, and it is still difficult to determine the difficulty of obtaining pure products; 3. Chemical synthesis: combined with adenosine Compared with the semi-synthetic method of synthesizing 3-deoxyribose and then synthesizing nucleosides, the semi-synthetic method as a starting material is generally shorter and the raw materials are easily available. This method is more suitable for large-scale production

However, the methods reported in the literature related to this synthesis idea have more or less defects of one kind or another—either the price is expensive, or the pollution is serious or the conditions are harsh, or the quality of the final product is difficult to guarantee that it meets the requirements for use in medicine or health care products.

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