Synthesis of P-chiral, phosphorothioic acid analogs of N-phospholeucinamide

被引：8
|
作者：
Thompson, CM [1 ]
Lin, J [1 ]
机构：
[1] LOYOLA UNIV,DEPT CHEM,CHICAGO,IL 60626
来源：
TETRAHEDRON LETTERS | 1996年 / 37卷 / 50期
关键词：
N-phospholeucinamide; phosphoramidothioic acid; stereoisomer;
D O I：
10.1016/S0040-4039(96)02107-7
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A diastereomeric mixture of R(p)- and S-p- N-[O-methyl phosphorothioic acid]leucinamides were synthesized by thiophosphorlation of leucinamide followed by monodealkylation of the phosphate methyl ester. Individual diastereomers were prepared by a sequence utilizing selective protection of the thioic acid moiety as the S-benzyl group, chromatographic separation, and deprotection. Copyright (C) 1996 Elsevier Science Ltd
引用
收藏
页码：8979 / 8982
页数：4
相关论文
共 50 条
  • [41] 1,3,2-Oxathiaphospholane approach to the synthesis of P-chiral stereodefined analogs of oligonucleotides and biologically relevant nucleoside polyphosphates
    Nawrot, Barbara
    Rebowska, Beata
    Michalak, Olga
    Bulkowski, Marek
    Blaziak, Damian
    Guga, Piotr
    Stec, Wojciech J.
    PURE AND APPLIED CHEMISTRY, 2008, 80 (08) : 1859 - 1871
  • [42] Synthesis and polymerization of optically active N-propargylphosphonamidates:: A novel helical polymer carrying a P-chiral center
    Yue, Dongmei
    Fujii, Toru
    Terada, Kayo
    Tabei, Junichi
    Shiotsuki, Masashi
    Sanda, Fumio
    Masuda, Toshio
    MACROMOLECULAR RAPID COMMUNICATIONS, 2006, 27 (17) : 1460 - 1464
  • [43] Catalytic asymmetric synthesis using P-chiral diaminophosphine oxide preligands: DIAPHOXs
    Nemoto, Tetsuhiro
    Hamada, Yasumasa
    TETRAHEDRON, 2011, 67 (04) : 667 - 687
  • [44] Enantioselective preparation of P-chiral phosphine oxide organocatalysts and their application in asymmetric synthesis
    Warner, Christopher J. A.
    Jones, Simon
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 243
  • [45] Palladium (II) promoted synthesis of p-chiral iminophosphines by the hydroamination of phosphinoalkynes.
    Liu, XM
    Mok, KF
    Vittal, JJ
    Leung, PH
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2001, 221 : U650 - U650
  • [46] Novel P-chiral bidentate phosphine ligands: synthesis and use in asymmetric catalysis
    Nettekoven, U
    Widhalm, M
    Kamer, PCJ
    vanLeeuwen, PWNM
    TETRAHEDRON-ASYMMETRY, 1997, 8 (19) : 3185 - 3188
  • [47] Synthesis of Optically Active Polymers Using P-Chiral Bisphosphines as Anionic Initiators
    Morisaki, Y.
    Saito, K.
    Imoto, H.
    Suzuki, K.
    Ouchi, Y.
    Chujo, Y.
    POLYMER SCIENCE SERIES A, 2009, 51 (11-12) : 1218 - 1228
  • [48] STEREOSPECIFIC SYNTHESIS OF P-CHIRAL DI(2'-O-DEOXYRIBONUCLEOSIDE)METHANEPHOSPHONATES
    LESNIKOWSKI, ZJ
    JAWORSKAMASLANKA, MM
    STEC, WJ
    NUCLEOSIDES & NUCLEOTIDES, 1991, 10 (1-3): : 733 - 736
  • [49] Synthesis of optically active polymers using P-chiral bisphosphines as anionic initiators
    Y. Morisaki
    K. Saito
    H. Imoto
    K. Suzuki
    Y. Ouchi
    Y. Chujo
    Polymer Science Series A, 2009, 51
  • [50] Nucleophilic aromatic substitution reactions of fluorobenzenechromium complexes with P-chiral secondary phosphine-boranes: synthesis of optically pure P-chiral (dialkyl)arylphosphine-boranes
    Katagiri, K
    Danjo, H
    Yamaguchi, K
    Imamoto, T
    TETRAHEDRON, 2005, 61 (19) : 4701 - 4707
12345