Stereoselective synthesis of fluorinated aminoglycosyl phosphonates

被引:17
|
作者
Bouwman, Sanne
Orru, Romano V. A.
Ruijter, Eelco [1 ]
机构
[1] Vrije Univ Amsterdam, Dept Chem & Pharmaceut Sci, NL-1081 HV Amsterdam, Netherlands
关键词
C-GLYCOSYLPHOSPHONATES; REAGENT SYSTEM; 2-NITROGLYCALS; BIOSYNTHESIS; GLYCALS; ANALOGS;
D O I
10.1039/c4ob02317j
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We describe the conjugate addition of lithiated difluoromethane-phosphonates to a diverse range of nitroglycals as a convenient method for the highly stereoselective synthesis of fluorinated aminoglycosyl phosphonates. Our approach provides opportunities to produce hydrolytically stable mimics of biologically important aminoglycosyl phosphates.
引用
收藏
页码:1317 / 1321
页数:5
相关论文
共 50 条
  • [41] A Highly Stereoselective Formal Synthesis of Hapalosin
    Kumar, Harish
    Reddy, A. Srinivas
    Yadav, J. S.
    Reddy, B. V. Subba
    SYNLETT, 2013, 24 (11) : 1415 - 1419
  • [42] Strategies for the Synthesis of Fluorinated Nucleosides, Nucleotides and Oligonucleotides
    Shet, Harshita
    Sahu, Rajesh
    Sanghvi, Yogesh S.
    Kapdi, Anant R.
    CHEMICAL RECORD, 2022, 22 (09)
  • [43] Solvent-and Catalyst-Free Reaction of (Aminomethyl)phosphonates with Epoxides: Synthesis of Novel {[(2-Hydroxyethyl) amino] methyl}phosphonates
    Kaboudin, Babak
    Sorbiun, Mina
    HETEROATOM CHEMISTRY, 2010, 21 (05) : 284 - 289
  • [44] Recent Progress in Synthesis and Applications of Fluorinated Carbohydrates
    Cheng, Yuan
    Guo, Ai-Ling
    Guo, Dian-Shun
    CURRENT ORGANIC CHEMISTRY, 2010, 14 (09) : 977 - 999
  • [45] Synthesis and antiviral evaluation of base-modified deoxythreosyl nucleoside phosphonates
    Liu, Chao
    Dumbre, Shrinivas G.
    Pannecouque, Christophe
    Korba, Brent
    De Jonghe, Steven
    Herdewijn, Piet
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (26) : 5513 - 5528
  • [46] Free Radical Hydrophosphorylation of Fluoroalkyl Vinyl Ethers: Synthesis of Fluoroalkyl Phosphonates
    Oparina, L. A.
    Khil'ko, M. Ya.
    Kolyvanov, N. A.
    Gusarova, N. K.
    Nedolya, N. A.
    Saprygina, V. N.
    Apartsyn, K. A.
    Kireeva, V. V.
    Trofimov, B. A.
    RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2020, 90 (04) : 614 - 618
  • [47] First Stereoselective and Concise Synthesis of Rhoiptelol C
    Reddy, Sudina Purushotham
    Chinnababu, Baggu
    Venkateswarlu, Yenamandra
    HELVETICA CHIMICA ACTA, 2014, 97 (07) : 999 - 1003
  • [48] Stereoselective synthesis of N-galactofuranosyl amides
    Nisic, Filippo
    Bernardi, Anna
    CARBOHYDRATE RESEARCH, 2011, 346 (04) : 465 - 471
  • [49] First stereoselective total synthesis of pectinolide H
    Ramesh, D.
    Shekhar, V.
    Chantibabu, D.
    Rajaram, S.
    Ramulu, U.
    Venkateswarlu, Y.
    TETRAHEDRON LETTERS, 2012, 53 (10) : 1258 - 1260
  • [50] Stereoselective synthesis of the cytotoxic macrolide aspergillide B
    Diaz-Oltra, Santiago
    Angulo-Pachon, Cesar A.
    Kneeteman, Maria N.
    Murga, Juan
    Carda, Miguel
    Alberto Marco, J.
    TETRAHEDRON LETTERS, 2009, 50 (27) : 3783 - 3785