(4R)-4-benzyloxycarbonylamino-3-oxo-hexanoic acid methyl ester | 147778-58-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (4R)-4-benzyloxycarbonylamino-3-oxo-hexanoic acid methyl ester
• 英文别名: methyl (4R)-(benzyloxycarbonylamino)-5-methyl-3-oxohexanoate；(4R)-4-Benzyloxycarbonylamino-5-methyl-3-oxo-hexanoic Acid Methyl Ester；methyl (4R)-5-methyl-3-oxo-4-(phenylmethoxycarbonylamino)hexanoate
• CAS: 147778-58-3
• 化学式: C₁₆H₂₁NO₅
• 分子量: 307.346
• InChiKey: XRKMJFBWDYVJRJ-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4R)-4-benzyloxycarbonylamino-3-oxo-hexanoic acid methyl ester 在 钾硼氢 作用下， 以 甲醇 为溶剂， 以77%的产率得到(3S,4R)-4-benzyloxycarbonylamino-3-hydroxyhexanoic acid methyl ester
  参考文献：
  名称：

  Total synthesis of (−)-tamandarin B

  摘要：

  The synthesis of tamandarin B is described. Key steps in the synthesis of the macrocycle component include a diastereoselective ketone reduction, linear precursor formation via an activated pentafluorophenyl ester, and HATU-promoted cyclization. Side-chain coupling was achieved in excellent yield with the newly developed coupling reagent DEPBT. (C) 2000 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(00)01409-x
• 作为产物：
  描述：

  D-缬氨酸 在 4-二甲氨基吡啶 、 碳酸氢钠 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (4R)-4-benzyloxycarbonylamino-3-oxo-hexanoic acid methyl ester
  参考文献：
  名称：

  Total Syntheses and Biological Investigations of Tamandarins A and B and Tamandarin A Analogs

  摘要：

  Tamandarins A (1) and B (2), two natural products similar in structure to didemnin B (3), were recently isolated from a Brazilian marine ascidian of the family Didemnidae. The cytotoxicity of 1 was reported to be somewhat more potent in vitro than that of 3 against various human cancer cell lines. The present account describes the first total syntheses of 1 and 2, and the syntheses of tamandarin A side chain analogues. The cytotoxicity data for these compounds show that the side chain modifications exhibit a parallel effect for both didemnins and tamandarins. This observation supports tamandarins' role as didemnins' mimic.

  DOI：

  10.1021/ja010222c

文献信息

• Enantioselective and Diastereoselective Formation of<i>syn</i>-3-Hydroxy-4-amino Acids (<i>syn</i>-Statines) via Tetramic Acids
  作者：Ulrich Schmidt、Bernd Riedl、Gerhard Haas、Helmut Griesser、Andrea Vetter、Steffen Weinbrenner

  DOI：10.1055/s-1993-25834

  日期：——

  Enantiomerically pure pyrrolidine-2,4-diones (tetramic acids) which can be diastereoselectively hydrogenated to syn-statines (4-amino-3-hydroxy-6-methylheptanoic acids) have been prepared by catalytic hydrogenation of 4-(benzyloxycarbonylamino)-3-oxocarboxylic acid esters.

  通过催化 4-(苄氧羰基氨基)-3-氧代羧酸酯的氢化反应，制备出了对映体纯的吡咯烷-2,4-二酮（四元酸），它可以非对映选择性地氢化为 syn-statines（4-氨基-3-羟基-6-甲基庚酸）。
• Tamandarin analogs and fragments thereof and methods of making and using
  申请人：Joullie M. Madeleine

  公开号：US20070149446A1

  公开（公告）日：2007-06-28

  The present invention is directed to a compound of Formula I wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , W, X, Y, and Z are defined herein. The compounds of the present invention are useful as anticancer agents. Specifically, the compounds are useful for treating or preventing cancer and tumor growth. The present invention is also directed to compositions comprising a compound according to the above formula. The present invention is also directed to methods of using a compound according to the above formula.

  本发明涉及公式I中R1、R2、R3、R4、R5、R6、W、X、Y和Z所定义的化合物。本发明的化合物可用作抗癌剂。具体而言，这些化合物可用于治疗或预防癌症和肿瘤生长。本发明还涉及包括上述公式中化合物的组合物。本发明还涉及使用上述公式中化合物的方法。
• US8030279B2
  申请人：——

  公开号：US8030279B2

  公开（公告）日：2011-10-04
• Total synthesis of (−)-tamandarin B
  作者：Madeleine M Joullié、Padma Portonovo、Bo Liang、David J Richard

  DOI：10.1016/s0040-4039(00)01409-x

  日期：2000.12

  The synthesis of tamandarin B is described. Key steps in the synthesis of the macrocycle component include a diastereoselective ketone reduction, linear precursor formation via an activated pentafluorophenyl ester, and HATU-promoted cyclization. Side-chain coupling was achieved in excellent yield with the newly developed coupling reagent DEPBT. (C) 2000 Published by Elsevier Science Ltd.
• Total Syntheses and Biological Investigations of Tamandarins A and B and Tamandarin A Analogs
  作者：Bo Liang、David J. Richard、Padma S. Portonovo、Madeleine M. Joullié

  DOI：10.1021/ja010222c

  日期：2001.5.1

  Tamandarins A (1) and B (2), two natural products similar in structure to didemnin B (3), were recently isolated from a Brazilian marine ascidian of the family Didemnidae. The cytotoxicity of 1 was reported to be somewhat more potent in vitro than that of 3 against various human cancer cell lines. The present account describes the first total syntheses of 1 and 2, and the syntheses of tamandarin A side chain analogues. The cytotoxicity data for these compounds show that the side chain modifications exhibit a parallel effect for both didemnins and tamandarins. This observation supports tamandarins' role as didemnins' mimic.