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XIONG Lun, GUAN Dongliang, LI Jian, HUANG Wei. Synthetic process of telavancin[J]. Journal of China Pharmaceutical University, 2017, 48(2): 172-177. DOI: 10.11665/j.issn.1000-5048.20170207
Citation: XIONG Lun, GUAN Dongliang, LI Jian, HUANG Wei. Synthetic process of telavancin[J]. Journal of China Pharmaceutical University, 2017, 48(2): 172-177. DOI: 10.11665/j.issn.1000-5048.20170207
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Synthetic process of telavancin

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    • Abstract
  • New process reported the synthesis of telavancin using decyl alcohol as the starting material. After methanesulfonylation, nucleophilic substitution with ethanolamine, Fmoc protection, and Parikh-Doering oxidation, the intermdiate N-(9-fluorenyl-9-methoxycarbonyl)decylaminoethyl acetaldehyde( 5 )was obtained. Vancomycin hydrochloride and intermediate 5 were then subject to reductive amination reaction, Fmoc deprotection, and Mannich reaction to give the telavancin product. The process have been deeply studied on the two key reactions of reductive amination and Mannich reaction, and the reaction conditions have been optimized. The overall yield is 46% based on starting material vancomycin.
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    • References (12)
  • [1]
    Chang MH,Kish TD,Fung HB.Telavancin:a lipoglycopeptide antimicrobial for the treatment of complicated skin and skin structure infections caused by Gram-positive bacteria in adults[J].Clin Ther,2010,32(13):2160-2185.
    [2]
    Karlowsky JA,Nichol K,Zhanel GG.Telavancin:mechanisms of action,in vitro activity,and mechanisms of resistance[J].Clin Infect Dis,2015,61(Suppl 2):S58-S68.
    [3]
    Hegde SS, Janc JW. Efficacy of telavancin, a lipoglycopeptide antibiotic,in experimental models of Gram-positive infection[J].Expert Rev Anti-Infe,2014,12(12):1463-1475.
    [4]
    Higgins DL,Chang R,Debabov DV,et al.Telavancin,a multifunctional lipoglycopeptide,disrupts both cell wall synthesis and cell membrane integrity in methicillin-resistant Staphylococcus aureus[J].Antimicrob Agents Chemother,2005,49(3):1127-1134.
    [5]
    Lee J, Liu J. Process for preparing glycopeptide phosphonate derivatives:US,7074890[P].2004-08-25[2016-04-04] .
    [6]
    Leadbetter MR.Glycopeptide phosphonate derivatives:US,8541375[P].2011-12-16[2016-04-04] .
    [7]
    Liang YH, Feng WH. Process improvement on the synthesis of lipoglycopeptide antibiotic telavancin[J].Chin J Synt Chem(合成化学),2011,19(4):550-553.
    [8]
    Ma S,Jia CY,Yuan H,et al.Synthesis of telavancin[J].Chin J New Drugs(中国新药杂志),2013,23(23):2809-2812.
    [9]
    Benito-Garagorri D. Process for the synthesis of telavancin, its pharmaceutically acceptable salts as well as an N-protected imine-derivative of telavancin:WO,2013034676[P].2011-09-09[2016-04-04] .
    [10]
    Li XP,Wu JP,Liang XM,et al.Application of DMSO as oxidant in organic syntheses[J].Chin J Org Chem(有机化学),2001,21(8):549-556.
    [11]
    Tidwell TT.Oxidation of alcohols by activated dimethyl sulfoxide and related reactions:an update[J].Synthesis,1990(10):857-870.DOI: 10.1002/chin.199112358.
    [12]
    Parikh JR,Doering WE.Sulfur trioxide in the oxidation of alcohols by dimethyl sulfoxide[J].J Am Chem Soc,1967,89(21):5505-5507.
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