Practical and scalable one-pot synthesis of arbekacin

被引:0
|
作者
Zhang, Hongsen [1 ]
Wang, Chunxiao [1 ]
Liu, Kai [1 ]
Li, Chao [1 ]
Qiao, Renzhong [1 ]
机构
[1] Beijing Univ Chem Technol, State Key Lab Chem Resource Engn, Beijing, Peoples R China
基金
中国国家自然科学基金;
关键词
Nuclear magnetic resonance spectroscopy;
D O I
10.1039/d3re00598d
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An efficient and scalable one-pot production process was developed to prepare arbekacin from dibekacin. The impurities derived from side chains at different NH2 sites were separated, and analyzed by ESI-HRMS2 and 2D NMR. The reactivities of NH2 were evaluated through DFT theoretical calculations to optimize the process conditions. Solvent polarity was found to be an important factor affecting the ratio of product to impurities, and the possible mechanism was investigated. This work gave a practical synthetic process of arbekacin, especially for large scale production. An efficient and scalable one-pot production process was developed to prepare arbekacin from dibekacin.
引用
收藏
页码:1179 / 1184
页数:6
相关论文
共 50 条
  • [21] A facile and practical one-pot 'catch and release' synthesis of substituted guanidines
    Wang, Ying
    Sauer, Daryl R.
    Djuric, Stevan W.
    TETRAHEDRON LETTERS, 2009, 50 (36) : 5145 - 5148
  • [22] A practical one-pot synthesis of 5-aryl-2-furaldehydes
    McClure, MS
    Roschangar, F
    Hodson, SJ
    Millar, A
    Osterhout, MH
    SYNTHESIS-STUTTGART, 2001, (11): : 1681 - 1685
  • [23] Practical One-Pot Synthesis of Protected L-Glyceraldehyde Derivatives
    Stecko, Sebastian
    Michalak, Michal
    Stodulski, Maciej
    Mucha, Lukasz
    Parda, Kamil
    Furman, Bartlomiej
    Chmielewski, Marek
    SYNTHESIS-STUTTGART, 2012, 44 (17): : 2695 - 2698
  • [24] A practical one-pot procedure for the synthesis of N-H isoquinolones
    Lu, Shaonan
    Lin, Yingfu
    Zhong, Hongban
    Zhao, Kang
    Huang, Jianhui
    TETRAHEDRON LETTERS, 2013, 54 (15) : 2001 - 2005
  • [25] A practical one-pot synthesis of O-unprotected glycosyl thioureas
    Maya, I
    López, O
    Fernández-Bolaños, JG
    Robina, I
    Fuentes, J
    TETRAHEDRON LETTERS, 2001, 42 (32) : 5413 - 5416
  • [26] Isothermal Suspension Conversion as a Route to Cocrystal Production: One-Pot Scalable Synthesis
    Croker, Denise M.
    Rasmuson, Ake C.
    ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2014, 18 (08) : 941 - 946
  • [27] One-pot synthesis of β-imidazolylpropionamides
    Ryabukhin, Sergey V.
    Granat, Dmitry S.
    Khodakovskiy, Pavel V.
    Shivanyuk, Alexander N.
    Tolmachev, Andrey A.
    TETRAHEDRON LETTERS, 2008, 49 (25) : 3997 - 4002
  • [28] A ONE-POT SYNTHESIS OF NITROENAMINES
    FAULQUES, M
    RENE, L
    ROYER, R
    SYNTHESIS-STUTTGART, 1982, (04): : 260 - 261
  • [29] One-pot synthesis of (−)-Ambrox
    Shaoxiang Yang
    Hongyu Tian
    Baoguo Sun
    Yongguo Liu
    Yanfeng Hao
    Yanyu Lv
    Scientific Reports, 6
  • [30] A ONE-POT SYNTHESIS OF AZOMETHANE
    REMMLER, M
    ONDRUSCHKA, B
    ZIMMERMANN, G
    JOURNAL FUR PRAKTISCHE CHEMIE, 1985, 327 (05): : 868 - 870