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Method for preparing epothilone D and B

A technology of epothilones and compounds, which is applied in the field of total synthesis of epothilones D and B, can solve the problems of low yield of epothilones, and achieve convenience for mass production, high yield, and few synthesis steps Effect

Inactive Publication Date: 2012-08-15
ACCENDATECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] The yield of epothilones produced by microbial fermentation is low, and only certain epothilone compounds can be produced

Method used

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  • Method for preparing epothilone D and B
  • Method for preparing epothilone D and B
  • Method for preparing epothilone D and B

Examples

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Comparison scheme
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Embodiment Construction

[0021] In order to understand the present invention, the present invention is further illustrated below with examples, but it is not intended to limit the protection scope of the present invention.

[0022] Synthesis of Epothilone D and B

[0023] Synthesis of (D)-Acetylcamphor-endesulphonamide (2)

[0024] Under the protection of nitrogen, add 4.1g sodium hydride (102.8mmol) into the round bottom flask, then add petroleum ether and stir for 30min, let stand, remove the supernatant, then add 500mL tetrahydrofuran into the round bottom flask and cool to 0°C, Add 20 g of camphor endosulphonamide (93.5 mmol) in 150 mL of tetrahydrofuran solution dropwise, stir for 1 h after the drop is complete, then add 8.3 mL of acetyl chloride (112.2 mmol) drop by drop, after the addition, the temperature rises to room temperature, stir overnight, after the reaction is complete Add 62mL of sodium bicarbonate aqueous solution (1.19M), stir for 20min, spin out most of THF, extract with ethyl ac...

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Abstract

The invention relates to a preparation method of epothilone D and B, which comprises the following steps: reacting carboxylic acid (6) and hydroxyl compound (7) to obtain an ester (8), reacting with a key intermediate (9) in an Aldol mode to obtain a compound (10), carrying out hydroxy protection with proper protective group to obtain a compound (11), carrying out RCM reaction to close the cycle to obtain a compound (12), removing the hydroxy protective group to obtain the compound epothilone D, and epoxidating to obtain the epothilone B.

Description

technical field [0001] The invention belongs to the technical field of medicines, and in particular relates to a total synthesis preparation method of epothilone D and B. The method provided by the invention has high reaction yield, simple operation and easy industrialization. Background technique [0002] The discovery of epothilone A and B was in the 1990s. Hofle and his colleagues first found a Sorangium cellulosum (Myxococcales) strain Soce90 from the soil on the banks of the Zambesi River in South Africa. A compound with antifungal activity was isolated from the plant and its properties were studied. Around 1995, Bollag et al. found that epothilone is a kind of tubulin polymerization-promoting property similar to p-glycotriol, which shows strong anti-tumor effect in multidrug-resistant tumor cell lines expressing p-glycoprotein. Tumor active, structurally novel anticytotoxic compounds. Moreover, it was found that the activity of natural epothilone is 10 to 1,000 times...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/06C07D493/04C07C47/21C07C45/56C07C57/03C07C51/285
CPCY02P20/55
Inventor 冯鹏
Owner ACCENDATECH
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