Patents Assigned to UNIVERSITY OF SHAOXING
  • Patent number: 9051254
    Abstract: 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 ?40˜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.
    Type: Grant
    Filed: June 11, 2012
    Date of Patent: June 9, 2015
    Assignees: HANGZHOU NORMAL UNIVERSITY, UNIVERSITY OF SHAOXING
    Inventors: Pengfei Zhang, Chao Shen, Runpu Shen, Wei Liu, Chunlei Wu
  • Patent number: 8697919
    Abstract: 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.
    Type: Grant
    Filed: April 6, 2011
    Date of Patent: April 15, 2014
    Assignees: Zhejiang Medicine Co., Ltd., Xinchang Pharmaceutical Factory, University of Shaoxing
    Inventors: Xuejun Lao, Runpu Shen, Weidong Ye, Xiaohua Song, Luo Liu, Chunlei Wu, Xiongsheng Sun, Siping Hu
  • Publication number: 20130046114
    Abstract: 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.
    Type: Application
    Filed: April 6, 2011
    Publication date: February 21, 2013
    Applicants: University of Shaoxing, Zhejiang Medicine Co., Ltd., Xinchang Pharmaceutic al Factory
    Inventors: Xuejun Lao, Runpu Shen, Weidong Ye, Xiaohua Song, Luo Liu, Chunlei Wu, Xiongsheng Sun, Siping Hu
  • Publication number: 20120330048
    Abstract: 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.
    Type: Application
    Filed: March 9, 2011
    Publication date: December 27, 2012
    Applicants: UNIVERSITY OF SHAOXING, ZHEJIANG MEDICINE CO., LTD. XINCHANG PHARMACEUTICAL FACTORY
    Inventors: Xuejun Lao, Runpu Shen, Weidong Ye, Xiaohua Song, Luo Liu, Chunlei Wu, Yibin Wu, Liujiang Hu
  • Publication number: 20120316366
    Abstract: 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 ?40˜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.
    Type: Application
    Filed: June 11, 2012
    Publication date: December 13, 2012
    Applicants: UNIVERSITY OF SHAOXING, HANGZHOU NORMAL UNIVERSITY
    Inventors: PENGFEI ZHANG, CHAO SHEN, RUNPU SHEN, WEI LIU, CHUNLEI WU