Synthesis of orthogonally protected enantiopure 2,9-diaminodecanedioic acid:: A model for a new general method for the synthesis of orthogonally protected α,α′-diaminodicarboxylic acids

被引:0
|
作者
Truchot, C [1 ]
Sasaki, NA [1 ]
机构
[1] CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France
关键词
D O I
暂无
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new method for the synthesis of orthogonally protected enantiopure alpha,alpha'-diaminodicarboxylic acids is described. A key step involves the Julia olefination of an aldehyde and a sulfone, both of which are derived from an optically pure dicarboxylic amino acid such as aspartic and glutamic acid. Straightforward synthesis of orthogonally protected 2,9-diaminodecanedioic acid is chosen to demonstrate the conciseness of this new versatile approach.
引用
收藏
页码:393 / 406
页数:14
相关论文
共 50 条
  • [41] New oxazole-based peptidomimetics: Useful building blocks for the synthesis of orthogonally protected macrocyclic scaffolds
    Mann, E
    Kessler, H
    ORGANIC LETTERS, 2003, 5 (24) : 4567 - 4570
  • [42] A concise and general methodology for the complete asymmetric synthesis of the orthogonally protected 2-amino-1,3,4-butanetriols (ABTs)
    Singh, OV
    Han, H
    TETRAHEDRON LETTERS, 2003, 44 (28) : 5289 - 5292
  • [43] Enantioselective synthesis of C2-functionalized, N-protected morpholines and orthogonally N,N′-protected piperazines via organocatalysis
    O'Reilly, Matthew C.
    Lindsley, Craig W.
    TETRAHEDRON LETTERS, 2012, 53 (13) : 1539 - 1542
  • [44] Chiral aminoalkyl cation equivalents -: 1 -: One-pot synthesis of orthogonally protected enantiopure S-(aminoalkyl)cysteine derivatives
    Bolognese, A
    Fierro, O
    Guarino, D
    Longobardo, L
    Caputo, R
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (01) : 169 - 173
  • [45] Synthesis of 1,2,4-oxadiazole-linked orthogonally urethane-protected dipeptide mimetics
    Sureshbabu, Vommina V.
    Hemantha, Hosahalli P.
    Naik, Shankar A.
    TETRAHEDRON LETTERS, 2008, 49 (35) : 5133 - 5136
  • [46] Enantioenriched Bifunctional Crotylsilanes for the Asymmetric Synthesis of Orthogonally Protected 2-Methyl-1,3-diols
    Kim, Dongeun
    Lee, Jae Seung
    Lozano, Lucia
    Kong, Suk Bin
    Han, Hyunsoo
    ORGANIC LETTERS, 2013, 15 (19) : 5142 - 5145
  • [47] Structural Diversity-Oriented Synthesis of Orthogonally Protected Cyclic Amino Acid Derivatives with Multiple Stereogenic Centers
    Nonn, Melinda
    Remete, Attila M.
    Kiss, Lorand
    HELVETICA CHIMICA ACTA, 2020, 103 (07)
  • [48] SnCl2-Catalyzed Acetalation/Selective Benzoylation Sequence for the Synthesis of Orthogonally Protected Glycosyl Acceptors
    Lv, Jian
    Liu, Chun-Yang
    Guo, Yang-Fan
    Feng, Guang-Jing
    Dong, Hai
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 2022 (33)
  • [49] Synthesis of orthogonally protected (R)- and (S)-2-methylcysteine via an enzymatic desymmeterization and curtius rearrangement
    Kedrowski, BL
    JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (13): : 5403 - 5406
  • [50] Synthesis of orthogonally protected pyrrole tricarboxylic acid derivatives: Versatile building blocks for pyrrole-containing compounds
    Schmuck, C
    Rupprecht, D
    Urban, C
    Walden, N
    SYNTHESIS-STUTTGART, 2006, 1 (01): : 89 - 96