Enantiomeric phosphonate analogs of the paclitaxel C-13 side chain

被引：19
|
作者：
Wróblewski, AE [1 ]
Piotrowska, DG [1 ]
机构：
[1] Med Univ Lodz, Fac Pharm, Inst Chem, PL-90151 Lodz, Poland
来源：
TETRAHEDRON-ASYMMETRY | 1999年 / 10卷 / 10期
关键词：
D O I：
10.1016/S0957-4166(99)00206-2
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
Both enantiomers of syn diethyl 2-(benzoylamino)-1-hydroxy-2-phenylethylphosphonate have been obtained by resolution via O-methylmandelate derivatives. Removal of the resolving ester moiety was easily achieved by ammonolysis with no trace of the retro-Abramov reaction. Absolute configurations of the enantiomeric phosphonate analogs were established from H-1 (the Trost model) and P-31 NMR data of the O-methylmandelate derivatives. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：2037 / 2043
页数：7
相关论文
共 50 条
  • [1] Enantiomeric phosphonate analogs of the docetaxel C-13 side chain
    Wróblewski, AE
    Piotrowska, DG
    TETRAHEDRON-ASYMMETRY, 2000, 11 (12) : 2615 - 2624
  • [2] Phosphonate analogs of N-benzoyl- and N-Boc-3-phenylisoserine, the taxol C-13 side chain
    Wróblewski, AE
    Piotrowska, DG
    TETRAHEDRON, 1998, 54 (28) : 8123 - 8132
  • [3] Chemoenzymatic synthesis of the C-13 side chain of paclitaxel (Taxol) and docetaxel (Taxotere)
    Hamamoto, H
    Mamedov, VA
    Kitamoto, M
    Hayashi, N
    Tsuboi, S
    TETRAHEDRON-ASYMMETRY, 2000, 11 (22) : 4485 - 4497
  • [4] Synthesis of new analogs of the C-13 docetaxel side chain by asymmetric aminohydroxylation
    Montiel-Smith, S
    Cervantes-Mejía, V
    Dubois, J
    Guénard, D
    Guéritte, F
    Sandoval-Ramírez, J
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2002, 2002 (14) : 2260 - 2264
  • [5] Utilization of a benzoyl migration to effect an expeditious synthesis of the paclitaxel C-13 side chain
    Hu, ZY
    Erhardt, PW
    ORGANIC PROCESS RESEARCH & DEVELOPMENT, 1997, 1 (05) : 387 - 390
  • [6] Utilization of a benzoyl migration to effect an expeditious synthesis of the paclitaxel C-13 side chain.
    Hu, ZY
    Erhardt, PW
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1997, 213 : 234 - MEDI
  • [7] HIGHLY STEREOCONTROLLED ASYMMETRIC SYNTHESES OF TAXOL AND TAXOTERE C-13 SIDE-CHAIN ANALOGS
    MUKAI, C
    KIM, IJ
    FURU, E
    HANAOKA, M
    TETRAHEDRON, 1993, 49 (37) : 8323 - 8336
  • [8] Synthesis of the c-13 side-chain of taxol
    Borah, Jagat C.
    Boruwa, Joshodeep
    Barua, Nabin C.
    CURRENT ORGANIC SYNTHESIS, 2007, 4 (02) : 175 - 199
  • [9] Toward an ab initio potential energy surface for paclitaxel: A C-13 isoserine side chain conformational study
    Janicki, Maciej
    Lozynski, Marek
    JOURNAL OF MOLECULAR GRAPHICS & MODELLING, 2017, 73 : 94 - 100
  • [10] A practical and efficient synthesis of taxol C-13 side chain
    Zhou, ZQ
    Mei, XG
    Chang, JL
    Feng, DJ
    SYNTHETIC COMMUNICATIONS, 2001, 31 (23) : 3609 - 3615
12345