Preparation technology of 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose

A technology of benzoyl and ribofuranose, applied in the preparation of sugar derivatives, sugar derivatives, sugar derivatives, etc., can solve the problems of high cost, high organic waste discharge, low product yield, etc., and achieve low cost , low content of nitrogen-containing organic matter, and high product yield

Inactive Publication Date: 2012-09-12
LIVZON GROUP CHANGZHOU KONY PHARMA
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are three synthetic routes of 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose, using D-ribose, inosine and guanosine as starting materials respectively, of which Synthesis of 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose with inosine and guanosine as starting materials will produce nitrogen-containing heterocyclic by-products, requiring Recycling, meanwhile, the obtained product is more difficult to guarantee to be the β-type of higher purity (that is, the acetoxy group at the 1-position is in the β position)
Currently widely used is the method developed by Recondon et al. who uses D-ribose as the starting material and prepares the target product through three-step reactions. The target product synthesized by this method is β-type, with a melting point of 130-132 °C However, the product yield of this method is low, the cost is high, and the discharge of organic waste is high

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  • Preparation technology of 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose

Examples

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Embodiment 1

[0018] A preparation process for 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose, comprising the following steps:

[0019] (1) Glycosidation reaction Add 5ml of thionyl chloride dropwise to 100ml of methanol, cool in an ice-water bath, stir for 10-15 minutes, add 10g of D-ribose, and carry out glycosidation reaction at 0-5°C for 8 hours. Sodium neutralized the hydrogen chloride in the system, continued to stir for 30 minutes, filtered, concentrated the filtrate under reduced pressure to remove methanol, and obtained 11 g of the concentrate glycoside;

[0020] (2) Benzoylation reaction Mix 11 g of glycosidate with 150 ml of ethyl acetate and 5 ml of pyridine, heat to dissolve, add 30 g of potassium carbonate, and add 30 ml of benzoyl chloride dropwise at 60-70°C to carry out benzoylation reaction. After the dropwise addition, keep warm for 6 hours, filter out the insoluble matter in the system, wash the filtrate and combine, wash with water and 1.5mol / L sulfuric acid solution i...

Embodiment 2

[0024] A preparation process for 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose, comprising the following steps:

[0025] (1) Glycosidation reaction Add 5ml of thionyl chloride dropwise to 100ml of methanol, cool in an ice-water bath, stir for 10-15 minutes, add 10g of D-ribose, and carry out glycosidation reaction at 0-5°C for 8 hours. Sodium neutralized the hydrogen chloride in the system, continued to stir for 30 minutes, filtered, concentrated the filtrate under reduced pressure to remove methanol, and obtained 11 g of the concentrate glycoside;

[0026] (2) Benzoylation reaction Mix 11 g of glycosidate with 150 ml of ethyl acetate and 5 ml of pyridine, heat to dissolve, add 30 g of potassium carbonate, add 30 ml of benzoyl chloride dropwise at 40-50°C to carry out benzoylation reaction, Keep warm for 8 hours after the dropwise addition, filter out the insoluble matter in the system, wash the filtrate and combine, wash with water and 1.5mol / L sulfuric acid solution in tur...

Embodiment 3

[0030] A preparation process for 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose, comprising the following steps:

[0031] (1) Glycosidation reaction Add 5ml of thionyl chloride dropwise to 100ml of methanol, cool in an ice-water bath, stir for 10-15 minutes, add 10g of D-ribose, and carry out glycosidation reaction at 0-5°C for 8 hours. Sodium neutralized the hydrogen chloride in the system, continued to stir for 30 minutes, filtered, concentrated the filtrate under reduced pressure to remove methanol, and obtained 11 g of the concentrate glycoside;

[0032] (2) Benzoylation reaction Mix 11g of glycosidate with 150ml of dichloroethane and 5ml of pyridine, heat to dissolve, add 30g of potassium carbonate, drop 30ml of benzoyl chloride at 40-50°C to carry out benzoylation reaction , keep warm for 6 hours after the dropwise addition, filter out the insoluble matter in the system, wash the filtrate and combine, wash with water and 1.5mol / L sulfuric acid solution successively, the...

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Abstract

The invention relates to the technical field of chemical synthesis, and especially relates to a preparation technology of 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose, which comprises a glycosilation reaction, a benzoylation reaction and an acetylation reaction. According to the invention, the low temperature glycosilation reaction is carried out at 0-5DEG C, so the generation of a pyranose ring is effectively reduced; the benzoylation reaction is carried out through adopting an inorganic weak base, so the raw material cost, and contents of nitrogen-containing organic matters in process wastewater are reduced; a cosolvent is added to an acetylation reaction system, so the solidification of glacial acetic acid is effectively inhibited, the fluidity of the reaction system is improved, and stirring can fully perform effects, and is in favor of smooth carrying-out of the reaction. The whole preparation technology which has the advantages of simple operation, high product yield, low cost, and low contents of the nitrogen-containing organic matters in the wastewater is suitable for industrialized production.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to the preparation process of 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose. Background technique [0002] Non-natural nucleoside compounds are analogues of natural nucleoside compounds, which have the effect of falsehood in the body, can interfere with or directly act on the metabolic process of nucleic acids, and block the biosynthesis of proteins and nucleic acids. and anti-tumor chemotherapeutics have a very important position. With the acceleration of research and development of such compounds, non-natural nucleoside compounds have gradually become an important means for people to conquer bacteria, viruses and cancer. [0003] The common structural feature of nucleoside compounds is mainly composed of sugar groups and bases, 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose is an important sugar The base material can be used to synthesize a variety of nucleoside dr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H13/08C07H1/00
Inventor 陈敖李鸣海陈争一俞军
Owner LIVZON GROUP CHANGZHOU KONY PHARMA
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