Synthesis of orthogonally protected (3R,4S)- and (3S,4S)-4,5-diamino-3-hydroxypentanoic acids

被引：0
|
作者：
Z. Czajgucki
P. Sowiński
R. Andruszkiewicz
机构：
[1] Department of Pharmaceutical Technology and Biochemistry,
[2] Technical University of Gdańsk,undefined
[3] Gdańsk,undefined
[4] Poland,undefined
来源：
Amino Acids | 2003年 / 24卷
关键词：
Keywords: Amino acids; Protecting groups; NMR spectroscopy;
D O I：
暂无
中图分类号：
学科分类号：
摘要：
 The paper describes two methods of the synthesis of ethyl (3R,4S)- and (3S,4S)-4-[(benzyloxycarbonyl)amino]-5-[(tert-butyloxycarbonyl)amino]-3-hydroxypentanoates, useful for the syntheses of edeine analogs. Differently N-protected (S)-2,3-diaminopropanoic acid was used as a substrate in both procedures. The absolute configuration of newly generated asymmetric carbon atoms C-3 in β-hydroxy-γ,δ-diamino products was assigned by means of 1H NMR spectroscopy after their transformation into corresponding piperidin-2-ones.
引用
收藏
页码：289 / 291
页数：2
相关论文
共 50 条
  • [1] Synthesis of orthogonally protected (3R,4S)- and (3S,4S)-4,5-diamino-3-hydroxypentanoic acids
    Czajgucki, Z
    Sowinski, P
    Andruszkiewicz, R
    [J]. AMINO ACIDS, 2003, 24 (03) : 289 - 291
  • [2] Chemoenzymatic synthesis of orthogonally protected (3R,4R)- and (3S,4S)-trans-3-amino-4-hydroxypyrrolidines
    Rodriguez-Rodriguez, Jesus A.
    Javier Quijada, F.
    Brieva, Rosario
    Rebolledo, Francisca
    Gotor, Vicente
    [J]. TETRAHEDRON, 2013, 69 (26) : 5407 - 5412
  • [3] SYNTHESES OF EDEINE ANTIBIOTICS AND THEIR ANALOGS .6. SYNTHESIS OF PROTECTED (3R,4S) AND (3S,4S)-4,8-DIAMINO-3-HYDROXYOCTANOIC ACID
    GUMIENIAK, J
    ANDRUSZKIEWICZ, R
    BOROWSKI, E
    [J]. POLISH JOURNAL OF CHEMISTRY, 1984, 58 (7-9) : 881 - 885
  • [4] AN EXPEDITIOUS SYNTHESIS OF (3S,4S)-STATINE AND (3S,4S)-CYCLOHEXYLSTATINE
    TAKEMOTO, Y
    MATSUMOTO, T
    ITO, Y
    TERASHIMA, S
    [J]. TETRAHEDRON LETTERS, 1990, 31 (02) : 217 - 218
  • [5] A novel, facile and diastereoselective synthesis of (3S, 4S) and (3R, 4S)-N-Me-AHPPA
    Reddy, GV
    Rao, GV
    Iyengar, DS
    [J]. CHEMISTRY LETTERS, 1999, (07) : 703 - 704
  • [6] Chemoenzymatic synthesis of (3S,4S)- and (3R,4R)-3-methoxy-4-methylaminopyrrolidine
    Kamal, A
    Shaik, AA
    Sandbhor, M
    Malik, MS
    Kaga, H
    [J]. TETRAHEDRON LETTERS, 2004, 45 (43) : 8057 - 8059
  • [7] Chemoenzymatic synthesis of (3R,4S)- and (3S,4R)-3-methoxy-4-methylaminopyrrolidine
    Kamal, Ahmed
    Shaik, Ahmad Ali
    Sandbhor, Mahendra
    Malik, M. Shaheer
    Azeeza, Shaik
    [J]. TETRAHEDRON-ASYMMETRY, 2006, 17 (20) : 2876 - 2883
  • [8] A HIGHLY STEREOSELECTIVE SYNTHESIS OF (3S,4S)-STATINE AND (3S,4S)-CYCLOHEXYLSTATINE
    TAKEMOTO, Y
    MATSUMOTO, T
    ITO, Y
    TERASHIMA, S
    [J]. CHEMICAL & PHARMACEUTICAL BULLETIN, 1991, 39 (09) : 2425 - 2428
  • [9] Total synthesis of (3S,4S,2′S)- and (3R,4R,2′S)-viridiofungin A triester
    Pollex, A
    Abraham, L
    Müller, J
    Hiersemann, M
    [J]. TETRAHEDRON LETTERS, 2004, 45 (37) : 6915 - 6918
  • [10] Stereocontrolled Synthesis of (1R,3R,4S)- and (1S,3R,4S)-3,4-diaminocyclopentanols
    Guan, YS
    Green, MA
    Bergstrom, DE
    [J]. SYNLETT, 1999, (04) : 426 - 428
12345