Zhejiang Medicine Co., Ltd. Xinchang Pharmaceutical Factory

Shaoxing University

Other

University of Shaoxing

Hangzhou Normal University

Runpu Shen

Weidong Ye

Xuejun Lao

Chunlei Wu

Xiaohua Song

Luo Liu

Xiaoyue Jiang

Shiqing Pi

Chunlei Lv

Pengfei Zhang

Chao Shen

Wei Liu

Guofeng Wu

Siping Hu

Yibin Wu

Liujiang Hu

Xiongsheng Sun

Zhigang Wu

Guoqi Yu

Kui Wang

Bin Xie

Hongjun Huang

The present invention describes a novel synthetic method for preparing the key intermediate 2,6,10-trimethyl-1,1-dialkoxy-3,5,9-undecatriene of lycopene. An existing synthetic method have some disadvantages that it is very difficult to gain the raw material dialkyl 4-methyl-5,5-diakoxy-1-pentene-1-phosphonate (10) because no effective synthetic method can be adopted, and furthermore the obtained target compound is composed of several cis/trans isomers. This invention relates to a process comprising a condensation step wherein a starting C10-phosphonate is changed to its carbanion completely at a temperature of &#x2212;40&#x2dc;30 under an atmosphere of a non-reactive gas in an organic solvent catalyzed by base, and then C4-dialkyl is added to undergo Wittig-Horner condensation. This invention affords all trans C14-acetal and this method is characterized with the advantages of simple procedure, easy access to raw material and low cost, which makes it has the value of industrial application.

Method of preparing 2,6,10-Trimethyl-1,1-dialkoxy-3,5,9-undecatriene used as an intermediate of lycopene

Provided are a linezolid intermediate and the preparation method thereof and a method for synthesizing linezolid. The structure of the intermediate is shown as formula F2, wherein the compound is prepared by a condensation reaction of (S)&#x2014;N-(3-chloro-2-hydroxy-1-propyl) acetamide and the compound shown in formula F4. In the preparation methods of the compound shown in formula F2 and linezolid, the reaction system is mild, side reactions are few and the product yield is high. 

Linezolid intermediate and method for synthesizing linezolid

The present invention relates to an intermediate (12) of lycopene of 2,6,10-trimethyl-1,1-dialkoxyl-3,5,9-undecantriene of formula, (12) and its intermediate of 4-methyl-5,5-dialkoxyl-1-pentenyl-1-phosphonic acid dialkyl ester of formula (10), and their preparation methods. The process route is simple, the starting materials are available easily, the cost is low, and it is valuable in industry.

Intermediate of lycopene and preparation method of intermediate thereof

The invention relates to a novel important lycopene intermediate 3,7,11-trimethyl-1,3,6,10-tetraene-dodecyl diethyl phosphonate. A current lycopene intermediate 2,4,6,10-tetra-double bond pentadec-carbon phosphonate is difficult to synthesize. The invention provides a novel intermediate, which has the following synthesis steps of: preparing 2,6,10-trimethyl-3,5,9-undecane triene-1-aldehyde from pseudoionone; preparing 2,6,10-trimethyl-2,5,9-undecane triene-1-aldehyde from the 2,6,10-trimethyl-3,5,9-undecane triene-1-aldehyde; and subjecting the 2,6,10-trimethyl-2,5,9-undecane triene-1-aldehyde and tetraethyl methylenediphosphonate to condensation reaction to obtain target product. The invention can generate novel intermediate from raw material pseudoionone only by four reactions, thus the reactions are easy to control and great industrial value are achieved.

Lycopene intermediate 1, 3, 6, 10-tetra-double bond pentadec-carbon phosphonate as well as preparation method and use thereof

The invention discloses an intermediate 1-methoxyl-2,6,10-trimethyl-1,3,5, 9-undec-tetraene, and a preparation method and uses thereof. In the synthesis method for the current lycopene intermediate 2-pos double bond C-14 aldehyde (2,6,10-trimethyl-2,5,9-undecatriene-1-aldehyde), expensive methyl iodide, polluting dimethyl sulphide and dangerous strong base are needed, so that the method is hardly applied to industrial production. The invention provides a new compound 1-methoxyl-2,6,10-trimethyl-1,3,5,9-undec-tetraene, and pure 2-pos double bond C-14 aldehyde can be prepared by hydrolyzing and refining the compound. The synthetic route is simplified and the great suitability for industrial production is achieved.

1-methoxyl-2, 6, 10-trimethyl-1, 3, 5, 9-undec-tetraene, and preparation method and uses thereof

The present invention relates to 2,6,10-trimethyl-3,5,9-undecatrienyl-1-aldehyde represented by formula (3), and a method for preparing this intermediate. The process route of the present invention is simple, the starting materials are available easily, and the cost is low.

Intermediate of lycopene and preparation method of intermediate

1,4,6,10-tetra-double bond pentadec-carbon phosphonate of formula (4), and preparation method thereof are provided. The preparation method comprises: reacting a pseudo ionone of formula (2) with sulfonium salt to prepare a epoxide of formula (9), and then reacting the epoxide of formula (9) with magnesium bromide to prepare a C-14 aldehyde of formula (3); condensing the C-14 aldehyde of formula (3) with tetra-alkyl methylene diphosphonate to obtain 1,4,6,10-tetra-double bond pentadec-carbon phosphonate of formula (4). Furthermore, the preparation method of lycopene via 1,4,6,10-tetra-double bond pentadec-carbon phosphonate of formula (4) is also provided. The present method has the advantages of short route, easily obtained raw materials, and low cost.

1,4,6,10-tetra-double bond pentadec-carbon phosphonate, preparation method thereof, and preparation method of lycopene using the same

1-Chloro-2-methyl-4-acyloxy-2-butene derivatives can be synthesized in good yields and high purity starting from isoprene and employing a chlorohydrin formation reaction in a system made of N-chloroisocyanuric acid derivatives and water, followed by esterification and rearrangement of the crude product mixture.

Method of manufacturing 1-chloro-2-methyl-4-acyloxy-2-butene derivatives

The invention relates to a process for producing all trans-vitamin A ester (I). According to the present invention, vitamin A ester (I) can simply be synthesized in good yields and high purity by the reaction of phosphonate compound (IV) with aldehyde (II) in an organic solvent in the presence of a base.

Process for producing vitamin A ester

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Zhejiang, China

Runpu Shen