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
  • [31] Synthesis of α-fluorinated phosphonates from α-fluorovinylphosphonates:: A new route to analogues of lysophosphatidic acid
    Xu, Y
    Qian, L
    Prestwich, GD
    ORGANIC LETTERS, 2003, 5 (13) : 2267 - 2270
  • [32] Synthesis of fluorinated acyclic nucleoside phosphonates with 5-azacytosine base moiety
    Pomeisl, Karel
    Krecmerova, Marcela
    Pohl, Radek
    Snoeck, Robert
    Andrei, Graciela
    TETRAHEDRON, 2019, 75 (39)
  • [33] Stereoselective Synthesis of Fluorinated 1,3-cis-Diaminocyclopentanes
    Pasco, Morgane
    Moumne, Roba
    Lecourt, Thomas
    Micouin, Laurent
    JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (12): : 5137 - 5142
  • [34] Aldolase-catalysed stereoselective synthesis of fluorinated small molecules
    Windle, Claire L.
    Berry, Alan
    Nelson, Adam
    CURRENT OPINION IN CHEMICAL BIOLOGY, 2017, 37 : 33 - 38
  • [35] Stereoselective synthesis of fluorinated building blocks: New synthetic strategies
    Fustero, Santos
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 242
  • [36] Efficient synthesis of P-chiral biaryl phosphonates by stereoselective intramolecular cyclization
    Xu, Guangqing
    Li, Minghong
    Wang, Shouliang
    Tang, Wenjun
    Organic Chemistry Frontiers, 2015, 2 (10): : 1342 - 1345
  • [37] Stereoselective synthesis of a-hydroxy phosphonates/a-amino phosphonates using manganese-proline derived catalytic system
    Kaur, Parminder
    Lim, Hyun
    Datilus, Vicklyn
    Teriak, Rania
    Chohan, Prianka
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 254
  • [38] Stereoselective reactions of hydroxy allylic phosphonates
    De la Cruz, A
    Shabany, H
    Spilling, CD
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1998, 216 : U591 - U591
  • [39] STEREOSELECTIVE SYNTHESIS OF RIBONUCLEOSIDE 3',5'-CYCLIC METHYL(PHENYL)PHOSPHONATES AND PHOSPHONOTHIOATES
    ROELEN, HCPF
    DEVROOM, E
    WANG, AHJ
    VANDERMAREL, GA
    VANBOOM, JH
    NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 1992, 11 (01): : 141 - 156
  • [40] Stereoselective reactions of allylic hydroxy phosphonates
    De la Cruz, MA
    Shabany, H
    Spilling, CD
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1999, 144 : 181 - 184