(3S,4R,5S)-4-benzyloxycarbonylamino-5-methyl-3-(triisopropylsilanyloxy) heptanoic acid methyl ester | 250039-49-7

• 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 methyl ester
• 英文别名: methyl (3S,4R,5S)-5-methyl-4-(phenylmethoxycarbonylamino)-3-tri(propan-2-yl)silyloxyheptanoate
• CAS: 250039-49-7
• 化学式: C₂₆H₄₅NO₅Si
• 分子量: 479.733
• InChiKey: QZHNOZWNOIUISQ-UMXIMWEHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.45
• 重原子数：
  33
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3S,4R,5S)-4-benzyloxycarbonylamino-5-methyl-3-(triisopropylsilanyloxy) heptanoic acid methyl ester 在 palladium on activated charcoal 吗啉 、 盐酸 、 4-二甲氨基吡啶 、 sodium hydroxide 、 四(三苯基膦)钯 、 氢气 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 、 bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate 、 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 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 生成 (5S,8S,12S,13R,16S,17R,20S,22aS)-16-Amino-13-((S)-sec-butyl)-12-hydroxy-5-isobutyl-8-isopropyl-20-(4-methoxy-benzyl)-17,21-dimethyl-tetradecahydro-9,18-dioxa-3a,6,14,21-tetraaza-cyclopentacyclohenicosene-4,7,10,15,19,22-hexaone
  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
• 作为产物：
  描述：

  (4R,5S)-4-benzyloxycarbonylamino-5-methyl-3-oxo-heptanoic acid methyl ester 在 2,6-二甲基吡啶 、 钾硼氢 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 (3S,4R,5S)-4-benzyloxycarbonylamino-5-methyl-3-(triisopropylsilanyloxy) heptanoic 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

• 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.