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Method for synthesizing (2R, 3R)-3-phenyl ethylene oxide formic ether

A technology of phenyloxirane formate and synthesis method, which is applied in the field of side chain synthesis of anti-cancer raw materials docetaxel and paclitaxel, can solve problems such as unsuitability, and achieve high safety and simple raw materials Easy to obtain, no effects of highly toxic compounds

Active Publication Date: 2012-09-26
无锡紫杉药业股份有限公司
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Problems solved by technology

Also not suitable for use in the pharmaceutical industry

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  • Method for synthesizing (2R, 3R)-3-phenyl ethylene oxide formic ether
  • Method for synthesizing (2R, 3R)-3-phenyl ethylene oxide formic ether
  • Method for synthesizing (2R, 3R)-3-phenyl ethylene oxide formic ether

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Embodiment Construction

[0028] Preferred embodiments of the present invention are described below, and it should be understood that the preferred embodiments described here are only used to illustrate and explain the present invention, and are not intended to limit the present invention.

[0029]

[0030] 1. Synthesis of (2R, 3R)-3-phenyloxirane ethyl carboxylate (compound 1):

[0031] 204g (2mol) of ethyl glyoxylate, 424.25g (2.5mol) of benzyl bromide, 13.6g of tetrabutylammonium hydrogen sulfate, 160g of sodium hydroxide, 75.2g (0.43mol) of sulfolane derivatives in 15 in a mixed solvent of acetonitrile and water (9:1). After stirring at room temperature for 40 hours, filter, evaporate acetonitrile, add 4 liters of ethyl acetate, extract with 2 liters of water, and concentrate the organic phase to obtain an oily substance. After passing through a silica gel column, the mobile phase was ethyl acetate and petroleum ether (1:6), to obtain 296.4 g of compound 1, and the ee value determined by HPLC w...

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Abstract

The invention relates to a method for synthesizing (2R, 3R)-3-phenyl ethylene oxide formic ether. Glyoxylate undergoes a coupling reaction with benzyl halide in a mixed solvent of an organic solvent and water in the presence of an enantiomer tetrahydrothiophene sulphone derivative serving as a catalyst and under the action of a phase transfer catalyst and an inorganic alkaline substance to form aproduct with high-optical activity selection, namely the (2R, 3R)-3-phenyl ethylene oxide formic ether, wherein R is lower alkyl having 1 to 4 carbon atoms, and X is chlorine, bromine or iodine atoms. The synthetic process has the advantages of mild reaction condition, simple and readily available required raw materials, high safety and no highly toxic compounds, and is suitable for large-scale synthesis.

Description

technical field [0001] The invention relates to a drug synthesis technology, in particular to a method for synthesizing side chains of anticancer raw materials docetaxel and paclitaxel. Background technique [0002] The synthesis of docetaxel is mainly through the 10-DAB protected by the 7,10 hydroxyl group and the side chain (1) (4S, 5R)-N-tert-butoxycarbonyl--2-p-methoxyphenyl-4-phenyl -5-carboxy-1,3-oxazolane can obtain docetaxel precursor through coupling reaction, and then deprotect to obtain docetaxel. [0003] [0004] wherein R is a protecting group. [0005] Paclitaxel can also be synthesized by the 7-hydroxyl protected DAB with the side chain (2)(4S,5R)-N-benzoyl-2-p-methoxyphenyl-4-phenyl-5-carboxy-1,3-oxazidine Heterocyclopentane can obtain paclitaxel precursor through coupling reaction, and then obtain paclitaxel after deprotection. [0006] [0007] wherein R is a protecting group. [0008] This shows that intermediate (3) is one of the indispensable ...

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Application Information

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IPC IPC(8): C07D303/40C07D301/02
CPCY02P20/52
Inventor 蔡强李隆秦月红冉秀琼蒋文君黄辉徐信保葛月兰
Owner 无锡紫杉药业股份有限公司
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