L-leucyl-L-prolyl-N,O-dimethyl-L-tyrosine-N-boc-O-SEM-L-threonine | 250039-52-2

• 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: L-leucyl-L-prolyl-N,O-dimethyl-L-tyrosine-N-boc-O-SEM-L-threonine
• 英文别名: 2-trimethylsilylethoxymethyl (2S,3R)-3-[(2S)-2-[[(2S)-1-[(2S)-2-amino-4-methylpentanoyl]pyrrolidine-2-carbonyl]-methylamino]-3-(4-methoxyphenyl)propanoyl]oxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoate
• CAS: 250039-52-2
• 化学式: C₃₇H₆₂N₄O₁₀Si
• 分子量: 751.006
• InChiKey: XWFDZURBULSCIQ-XPTOATBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.11
• 重原子数：
  52
• 可旋转键数：
  22
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  176
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  L-leucyl-L-prolyl-N,O-dimethyl-L-tyrosine-N-boc-O-SEM-L-threonine 在 palladium on activated charcoal 盐酸 、 4-二甲氨基吡啶 、 氢气 、 N,N-二异丙基乙胺 、 3-(二乙氧基邻酰氧基)-1,2,3-苯并三嗪-4-酮 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 、 magnesium bromide 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 生成 tamandarin B
  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：

  Z-leucylprolyl-N,O-dimethyltyrosine-O-Boc-threonine-OSEM 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 以98%的产率得到L-leucyl-L-prolyl-N,O-dimethyl-L-tyrosine-N-boc-O-SEM-L-threonine
  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

• 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.
• 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).
• 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.