N-Z-D-valine pentafluorophenyl ester | 325687-63-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-Z-D-valine pentafluorophenyl ester
• 英文别名: (2,3,4,5,6-pentafluorophenyl) (2R)-3-methyl-2-(phenylmethoxycarbonylamino)butanoate
• CAS: 325687-63-6
• 化学式: C₁₉H₁₆F₅NO₄
• 分子量: 417.332
• InChiKey: KUEDKGYYWUVGRT-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N-Z-D-valine pentafluorophenyl ester 在 钾硼氢 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 (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 二氯甲烷 为溶剂， 生成 N-Z-D-valine pentafluorophenyl 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

• MARTYNOV, V. F.;POZDNEV, V. F.;SMIRNOV, A. O.;SOROCHINSKAYA, E. I., ZH. OBSHCH. XIMII, 60,(1990) N, S. 451-455
  作者：MARTYNOV, V. F.、POZDNEV, V. F.、SMIRNOV, A. O.、SOROCHINSKAYA, E. I.

  DOI：——

  日期：——
• 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.