tert-butyl N-[(3S,6S,10S,11R,14S,15R,18S,21S)-11-[(2S)-butan-2-yl]-18-[(4-methoxyphenyl)methyl]-15,19-dimethyl-3-(2-methylpropyl)-2,5,8,13,17,20-hexaoxo-6-propan-2-yl-10-tri(propan-2-yl)silyloxy-7,16-dioxa-1,4,12,19-tetrazabicyclo[19.3.0]tetracosan-14-yl]carbamate | 250039-55-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: tert-butyl N-[(3S,6S,10S,11R,14S,15R,18S,21S)-11-[(2S)-butan-2-yl]-18-[(4-methoxyphenyl)methyl]-15,19-dimethyl-3-(2-methylpropyl)-2,5,8,13,17,20-hexaoxo-6-propan-2-yl-10-tri(propan-2-yl)silyloxy-7,16-dioxa-1,4,12,19-tetrazabicyclo[19.3.0]tetracosan-14-yl]carbamate
• CAS: 250039-55-5
• 化学式: C₅₃H₈₉N₅O₁₂Si
• 分子量: 1016.4
• InChiKey: QPHPVTFLIDOWIE-NKGMAUKRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.47
• 重原子数：
  71
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  208
• 氢给体数：
  3
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[(3S,6S,10S,11R,14S,15R,18S,21S)-11-[(2S)-butan-2-yl]-18-[(4-methoxyphenyl)methyl]-15,19-dimethyl-3-(2-methylpropyl)-2,5,8,13,17,20-hexaoxo-6-propan-2-yl-10-tri(propan-2-yl)silyloxy-7,16-dioxa-1,4,12,19-tetrazabicyclo[19.3.0]tetracosan-14-yl]carbamate 在 N-甲基吗啉 、 盐酸 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 生成 tamandarin A
  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：

  O-((S)-2-((S)-1-(((S)-2-(((3S,4R,5S)-4-(((benzyloxy)carbonyl)amino)-5-methyl-3-((triisopropylsilyl)oxy)heptanoyl)oxy)-3-methylbutanoyl)-L-leucyl)-N-methylpyrrolidine-2-carboxamido)-3-(4-methoxyphenyl)propanoyl)-N-(tert-butoxycarbonyl)-L-threonine 在 palladium on activated charcoal 氢气 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 甲醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 tert-butyl N-[(3S,6S,10S,11R,14S,15R,18S,21S)-11-[(2S)-butan-2-yl]-18-[(4-methoxyphenyl)methyl]-15,19-dimethyl-3-(2-methylpropyl)-2,5,8,13,17,20-hexaoxo-6-propan-2-yl-10-tri(propan-2-yl)silyloxy-7,16-dioxa-1,4,12,19-tetrazabicyclo[19.3.0]tetracosan-14-yl]carbamate
  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