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Production process for preparing 1-oxy-acetyl-2,3,5-3-benzoyl-beta-Lribofuranose

A ribofuranose and benzoyl technology, applied in the direction of sugar derivatives, sugar derivatives, esterified saccharides, etc.

Inactive Publication Date: 2008-10-01
CHENGDA PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there have been many reports in the literature on the protection methods of various hydroxyl groups of sugars, but there are few processes suitable for industrial production.

Method used

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  • Production process for preparing 1-oxy-acetyl-2,3,5-3-benzoyl-beta-Lribofuranose
  • Production process for preparing 1-oxy-acetyl-2,3,5-3-benzoyl-beta-Lribofuranose
  • Production process for preparing 1-oxy-acetyl-2,3,5-3-benzoyl-beta-Lribofuranose

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Embodiment Construction

[0014] The present invention will be further described below by way of examples.

[0015] Step 1: Using L-ribose, methanol, hydrogen chloride, etc. as raw materials, synthesize 1-oxo-methyl-L-ribofuranose (I) through methylation. The mass ratio of L-ribose to methanol is 1:10-16, such as 1:12 or 1:14, preferably 1:12-13, and stirred at room temperature. After all the raw materials are dissolved, cool to -10°C and slowly introduce hydrogen chloride gas in an amount of 25% to 50% of the mass of L-ribose, such as 27% or 35% or 40%, most preferably 30% to 35%. After passing through, the reaction temperature is controlled at -15°C to 5°C, preferably -10°C to 1°C, and stirred for 10 to 18 hours, preferably 13 to 15 hours. TLC and HPLC tracked until the reaction of raw materials was complete. Slowly add pyridine with the same mass as ribose, stir and neutralize for 30 minutes. The crude product of 1-oxo-methyl-L-ribofuranose (I) can be obtained in a quantitative yield by high-vacu...

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Abstract

The method discloses a production technique for preparing 1-oxo-acetyl-2, 3, 5-tri-oxo-benzoyl-beta-L-ribofuranose, which has the advantages of high yield, simple post treatment and purification, etc., and is suitable for industrial production. The production technique comprises the following three steps that: step 1: L-ribose, methanol and hydrogen chloride are adopted as raw materials which are methylated and synthesized into 1-oxo-methyl-L-ribofuranose (I); step 2: 1-oxo-methyl-L-ribofuranose (I) and benzoyl chloride are adopted as raw materials which are esterified and systhesized into 1-oxo-methyl-2, 3, 5-tri-oxo-benzoyl-L-ribofuranose (II); step 3: the 1-oxo-methyl-2, 3, 5-tri-oxo-benzoyl-L-ribofuranose (II) and anhydride acetic acid are adopted as raw materials which are acetylated into 1-oxo-acetyl-2, 3, 5-tri-oxo-benzoyl-beta-L-ribofuranose (III).

Description

technical field [0001] The invention relates to a production process of a pharmaceutical intermediate, in particular to a production process for preparing 1-oxo-acetyl-2,3,5-tri-oxo-benzoyl-β-L-ribofuranose. Background technique [0002] Ribose and its derivative deoxyribose are an important part of nucleic acid, and also a component of some vitamins and coenzymes. D-ribose and its derivatives widely exist in natural compounds in the form of furan, while the enantiomer of D-ribose, L-ribose, does not exist in nature and can only be obtained through synthetic methods. Ribonucleosides and deoxyribonucleosides are an important class of antiviral agents. In recent years, reports on the application of L-ribose and its derivatives in medicine are increasing. The reason is that L-ribonucleosides have significant antiviral activity while being less toxic than D-ribonucleosides. Nucleoside derivatives formed by some L-ribose and derivatives deoxyribose and organic bases such as ad...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H13/06
Inventor 葛建利谢南生
Owner CHENGDA PHARM CO LTD
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