Synthesis method of mannosidase inhibitor Kifunensine

A mannosidase and synthesis method technology, applied in the field of compound synthesis, can solve the problems of generating a large amount of impurities, high market price, unfavorable purification, etc., and achieve the effects of high overall reaction yield, good industrialization prospects, and cheap and easily available reagents

Inactive Publication Date: 2019-09-20
TIANJIN INT JOINT ACADEMY OF BIOTECH & MEDICINE
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] At present, there are fewer methods for synthesizing Kifunensine. People such as P.A.Benjes have reported a kind of synthetic route (US20040063973A1) with N-acetyl-D-mannosamine as the starting material. The method has 8 steps of reaction conversion, and the total The yield is relatively high, but the reproducibility of this route is poor, especially in the step of oxidative ring

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  • Synthesis method of mannosidase inhibitor Kifunensine
  • Synthesis method of mannosidase inhibitor Kifunensine
  • Synthesis method of mannosidase inhibitor Kifunensine

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Embodiment Construction

[0045] Unless otherwise defined, the technical terms used in the following embodiments have the same meaning as commonly understood by those skilled in the art to which the present invention belongs. The test reagents used in the following examples, unless otherwise specified, are conventional biochemical reagents; the experimental methods, unless otherwise specified, are conventional methods.

[0046] The present invention has chosen the synthesis process under preferred conditions to illustrate the specific synthesis method of the compound molecules involved in the present invention, wherein the substituent R 1 Choose acetyl, substituent R 2 Choose tert-butyldiphenyl, substituent R 3 The pivaloyl group is selected, but the selection of the examples does not imply any limitation of the preparation method of the present invention.

[0047] 1. Synthesis of Intermediate 2

[0048]

[0049]20g (112.3mmol) L-gulonic acid-γ-lactone 1 and 1.93g (11.2mmol) p-toluenesulfonic aci...

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Abstract

The invention provides a synthesis method of mannosidase inhibitor Kifunensine. L-gulonic acid-gamma-lactone, which is cheap and easily available, is taken as an initial raw material to efficiently obtain the Kifunensine through multi-step chemical conversion, the overall yield of the reaction is high, reagents used in the process are cheap and easily available, and multiple steps in the synthesis process can be fed by a one-pot method, so that the operation is simple and convenient, and the method has a better industrial prospect.

Description

technical field [0001] The invention belongs to the technical field of compound synthesis, and in particular relates to a synthesis method of Kifunensine, a mannosidase inhibitor. Background technique [0002] Kifunensine (structural formula shown below) is an alkaloid isolated from the actinomycetes called Kitasatosporia kifunense. It is a neutral, stable compound. Kifunensine is a potent inhibitor of mannosidase I, compared to other mannosidase inhibitors such as deoxymannan, it rapidly penetrates into cells where it prevents endoplasmic reticulum mannosidase I (ERM) repairs mannose residues in precursor glycoproteins, thereby inhibiting glycosylation, while it has no inhibitory effect on mannosidase II and has a weak inhibitory effect on aryl mannosidase. Therefore, when incorporated into the cell culture medium, Kifunensine has no effect on cell growth or glycoprotein production, and can greatly improve the quality and expression of the prepared glycoprotein. Based on...

Claims

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Application Information

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IPC IPC(8): C07D471/04
CPCC07D471/04Y02P20/55
Inventor 蔡岩袁昊林吴玉保杨阳郭宇汪颖赵佩佩贺万丽
Owner TIANJIN INT JOINT ACADEMY OF BIOTECH & MEDICINE
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