(3S,4R,5S)-4-Benzyloxycarbonylamino-5-methyl-3-triisopropylsilanyloxy-heptanoic acid (S)-1-allyloxycarbonyl-2-methyl-propyl ester | 250039-51-1

• 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: (3S,4R,5S)-4-Benzyloxycarbonylamino-5-methyl-3-triisopropylsilanyloxy-heptanoic acid (S)-1-allyloxycarbonyl-2-methyl-propyl ester
• 英文别名: [(2S)-3-methyl-1-oxo-1-prop-2-enoxybutan-2-yl] (3S,4R,5S)-5-methyl-4-(phenylmethoxycarbonylamino)-3-tri(propan-2-yl)silyloxyheptanoate
• CAS: 250039-51-1
• 化学式: C₃₃H₅₅NO₇Si
• 分子量: 605.888
• InChiKey: CAKSMLXLIJLSIG-XRCDWDDJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.58
• 重原子数：
  42
• 可旋转键数：
  21
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (3S,4R,5S)-4-Benzyloxycarbonylamino-5-methyl-3-triisopropylsilanyloxy-heptanoic acid (S)-1-allyloxycarbonyl-2-methyl-propyl ester 在 palladium on activated charcoal 、 四(三苯基膦)钯 吗啉 、 4-二甲氨基吡啶 、 氢气 、 magnesium bromide ethyl etherate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 17.5h， 生成 (2S,3R)-3-[(2S)-2-[[(2S)-1-[(2S)-2-[[(2S)-2-[(3S,4R,5S)-4-amino-5-methyl-3-tri(propan-2-yl)silyloxyheptanoyl]oxy-3-methylbutanoyl]amino]-4-methylpentanoyl]pyrrolidine-2-carbonyl]-methylamino]-3-(4-methoxyphenyl)propanoyl]oxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoic acid
  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：

  L-缬氨酸 在 四丁基碘化铵 4-二甲氨基吡啶 、 硫酸 、 potassium carbonate 、 N,N'-二环己基碳二亚胺 、 sodium nitrite 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 1.0h， 生成 (3S,4R,5S)-4-Benzyloxycarbonylamino-5-methyl-3-triisopropylsilanyloxy-heptanoic acid (S)-1-allyloxycarbonyl-2-methyl-propyl 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

• 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).