(2R,3S)-2-Benzyloxycarbonylamino-3-methyl-pentanoic acid pentafluorophenyl ester | 250039-48-6

• 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: (2R,3S)-2-Benzyloxycarbonylamino-3-methyl-pentanoic acid pentafluorophenyl ester
• 英文别名: (2,3,4,5,6-pentafluorophenyl) (2R,3S)-3-methyl-2-(phenylmethoxycarbonylamino)pentanoate
• CAS: 250039-48-6
• 化学式: C₂₀H₁₈F₅NO₄
• 分子量: 431.359
• InChiKey: CTLNPOOMSUWDMD-DYZYQPBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  (2R,3S)-2-Benzyloxycarbonylamino-3-methyl-pentanoic acid pentafluorophenyl ester 在 钾硼氢 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.58h， 生成 (3S,4R,5S)-4-benzyloxycarbonylamino-3-hydroxy-5-methyl-heptanoic acid methyl ester
  参考文献：
  名称：

  The First Total Synthesis of (−)-Tamandarin A

  摘要：

  [GRAPHICS]Tamandarin A (1), a newly isolated natural product similar in structure to didemnin a (2), was shown to be somewhat more active in vitro than 2 against pancreatic carcinoma with an ED50 value 1.5 to 2 ng/mL. We report here the first total synthesis of 1. The key steps include a practical stereoselective synthesis of the Hiv-isostatine unit, high-yielding linear precursor formation, a successful macrocyclization, and coupling of the macrocycle with the side chain to afford tamandarin A (1).

  DOI：

  10.1021/ol9910058
• 作为产物：
  描述：

  苯甲氧羰酰琥珀酰亚胺 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.5h， 生成 (2R,3S)-2-Benzyloxycarbonylamino-3-methyl-pentanoic acid pentafluorophenyl ester
  参考文献：
  名称：

  The First Total Synthesis of (−)-Tamandarin A

  摘要：

  [GRAPHICS]Tamandarin A (1), a newly isolated natural product similar in structure to didemnin a (2), was shown to be somewhat more active in vitro than 2 against pancreatic carcinoma with an ED50 value 1.5 to 2 ng/mL. We report here the first total synthesis of 1. The key steps include a practical stereoselective synthesis of the Hiv-isostatine unit, high-yielding linear precursor formation, a successful macrocyclization, and coupling of the macrocycle with the side chain to afford tamandarin A (1).

  DOI：

  10.1021/ol9910058

文献信息

• 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.
• The First Total Synthesis of (−)-Tamandarin A
  作者：Bo Liang、Padma Portonovo、Matthew D. Vera、Dong Xiao、Madeleine M. Joullié

  DOI：10.1021/ol9910058

  日期：1999.10.1

  [GRAPHICS]Tamandarin A (1), a newly isolated natural product similar in structure to didemnin a (2), was shown to be somewhat more active in vitro than 2 against pancreatic carcinoma with an ED50 value 1.5 to 2 ng/mL. We report here the first total synthesis of 1. The key steps include a practical stereoselective synthesis of the Hiv-isostatine unit, high-yielding linear precursor formation, a successful macrocyclization, and coupling of the macrocycle with the side chain to afford tamandarin A (1).