Method for preparing high-purity 5-deoxy-D-ribose

Abstract

The invention discloses a preparation method of high-purity 5-deoxy-D-ribose, and belongs to the technical field of chemical manufacturing and separation. According to the technical scheme, the preparation method comprises the following steps of carrying out an acylation reaction on 2,3-O-isopropylidene-D-methyl furanoside at 120 DEG C, and after the reaction is ended, obtaining an intermediate A;recrystallizing 1 part of the intermediate A with 5-20 parts by mass of a mixed solvent which is composed of isopropanol and methanol in a mass ratio of 5: 1, and after recrystallization and purification, obtaining an intermediate B; and carrying out an ammonolysis reaction on the intermediate B at the reaction temperature, and after the reaction is finished, carrying out post-treatment to obtainthe 5-deoxy-D-ribose. Compared with the prior art, the method has the advantages of simple synthesis route, accessible raw materials, mild technique conditions, lower cost and convenience for industrial production. The content of the 5-deoxy-D-ribose prepared by the method reaches 99% or above, so that the purity is high.

Description

technical field [0001] The invention relates to a method for preparing high-purity 5-deoxy-D-ribose, belonging to the technical field of chemical manufacturing and separation. Background technique [0002] Among anti-tumor and anti-viral drugs, a large number of nucleoside compounds are used clinically, and they are based on the principle of metabolic antagonism. Anti-disease effects are produced by interfering or inhibiting the nucleic acid replication of viruses and tumor cells. Usually biologically active nucleosides require the presence of a 5-hydroxyl group and function through phosphorylation in vivo. Removal of the 5-hydroxyl group yields a series of compounds of interest for biochemical and physiological studies. 5-deoxy-D-ribose is an important precursor of nucleoside drugs, widely used in antiviral and antitumor drugs, such as 5-deoxy-5-fluorouridine, 5-deoxythymidine, 5-deoxyadenosine , Capecitabine (Capecitabine), etc. [0003] D-ribose has hydroxyl groups at...

AI Technical Summary

Problems solved by technology

[0004] The synthesis technology of 5-deoxy-D-ribose is difficult

[0005] The main problem of synthesizing 5-deoxy-D-ribose is that the separation method is difficult, as "Kiss J D, Souza R, et al. Helv Chim Acta, 1982, 65 (5): 1522-1537", "Kissman H M, Baker B R.J Am Chem Soc, 1957, 79: 5534-5540", using D-ribose as raw material, after hydroxyl protection, halogenation (bromo or iodo), column separation after reduction dehalogenation; "Wang Xiangcheng, Wang Gang, Qu Ganglian .Chemical World, 2008, 4: 226-228 "improved the synthesis method of 5-deoxy-D-ribose, using D-ribose as raw material, protected by acetone / methanol to form 2,3-O-isopropylidene Base-D-furan-type methyl glycoside, after iodination of methyl iodide, catalytic hydrogenation, hydrolysis under acidic cationic resin conditions, to obtain 5-deoxy-D-ribose, but the column separation problem of the final product is still not solved

The column separation efficiency is low, a large amount of eluent is required, the energy consumption is large, time-consuming and laborious, and it is difficult for industrial application

[0006] The current commercially available 5-deoxy-D-ribose content is 95%-98%, which is expensive and largely limited by production capacity and separation technology

During the synthesis process of ribose compounds, the post-treatment is relatively difficult, easy to syrup, and the separation and purification methods have always been difficult