A practical synthesis of (-)fosfomycin from its enantiomer

被引:2
|
作者
Zhang, Meng [1 ]
Yu, Zheng [1 ]
Li, Ji Jun [1 ]
Yin, Da Li [2 ]
机构
[1] Beijing Collab Pharma Co Ltd, Beijing 102600, Peoples R China
[2] Peking Union Med Coll, Inst Mat Med, Beijing 100050, Peoples R China
关键词
Fosfomycin; Enantiomer; Phosphonate;
D O I
10.1016/j.cclet.2008.07.020
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(+)-cis-(1S, 2R)-Epoxypropylphosphonic acid, the enantiomer of fosfomycin, which is the industrial side-product in the preparation of the antibiotic fosfomycin, was converted into (-)fosfomycin by a seven-step procedure. The esterification of the dihydroxyphosphonic intermediate was the key step. The title compound was obtained in good yield and its optical purity was up to the medicine quality standard of Chinese Pharmacopoeia. (C) 2008 Meng Zhang. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.
引用
收藏
页码:1297 / 1300
页数:4
相关论文
共 50 条
  • [1] A practical synthesis of (-)fosfomycin from its enantiomer
    Meng Zhang~(a
    Chinese Chemical Letters, 2008, (11) : 1297 - 1300
  • [2] A practical synthesis of S-quinuclidine-2-carboxylic acid and its enantiomer
    Mi, Y
    Corey, EJ
    TETRAHEDRON LETTERS, 2006, 47 (15) : 2515 - 2516
  • [3] SYNTHESIS OF EVERNITROSE AND ITS ENANTIOMER
    YOSHIMURA, J
    MATSUZAWA, M
    SATO, KI
    FUNABASHI, M
    CHEMISTRY LETTERS, 1977, (12) : 1403 - 1406
  • [4] Catalytic asymmetric synthesis of Japonilure and its enantiomer
    Xu, Hao
    Li, Shuo-Ning
    Yang, Yan-Qing
    Zhou, Yun
    Yang, Qian-Zhen
    Bian, Qing-Hua
    Zhong, Jiang-Chun
    Wang, Min
    TETRAHEDRON-ASYMMETRY, 2014, 25 (20-21) : 1372 - 1375
  • [5] First total synthesis of Macrotricolorin A and its enantiomer
    Tanguturi, Prakash Gupta
    Gangapuram, Balraju
    Kashamalla, Chinna Ashalu
    Yadav, Jhillu Singh
    NATURAL PRODUCT RESEARCH, 2024,
  • [6] A short and efficient synthesis of (+)-disparlure and its enantiomer
    Koumbis, AE
    Chronopoulos, DD
    TETRAHEDRON LETTERS, 2005, 46 (25) : 4353 - 4355
  • [7] THE TOTAL SYNTHESIS OF (+/-) COMPACTIN AND ITS NATURAL (+) ENANTIOMER
    GIROTRA, NN
    WENDLER, NL
    TETRAHEDRON LETTERS, 1982, 23 (52) : 5501 - 5504
  • [8] The Asymmetric Total Synthesis of (-)-Eurothiocin A and Its Enantiomer
    Zhang, Guangyan
    Pan, Xuan
    Yang, Beibei
    Li, Li
    Liu, Zhanzhu
    JOURNAL OF NATURAL PRODUCTS, 2022, 85 (04): : 997 - 1005
  • [9] o-Bornylphenol: Stereochemistry and synthesis of new derivatives from its (+)-enantiomer
    Buravlev, E. V.
    Chukicheva, I. Yu
    Shumova, O. A.
    Suponitskii, K. Yu
    Kutchin, A. V.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 49 (09) : 1300 - 1306
  • [10] o-Bornylphenol: Stereochemistry and synthesis of new derivatives from its (+)-enantiomer
    E. V. Buravlev
    I. Yu. Chukicheva
    O. A. Shumova
    K. Yu. Suponitskii
    A. V. Kutchin
    Russian Journal of Organic Chemistry, 2013, 49 : 1300 - 1306