tert-butyl N-[(3S,6S,10S,11R,14S,15R,18S,21S)-18-[(4-methoxyphenyl)methyl]-15,19-dimethyl-3-(2-methylpropyl)-2,5,8,13,17,20-hexaoxo-6,11-di(propan-2-yl)-10-tri(propan-2-yl)silyloxy-7,16-dioxa-1,4,12,19-tetrazabicyclo[19.3.0]tetracosan-14-yl]carbamate | 325687-71-6

• 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)-18-[(4-methoxyphenyl)methyl]-15,19-dimethyl-3-(2-methylpropyl)-2,5,8,13,17,20-hexaoxo-6,11-di(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: 325687-71-6
• 化学式: C₅₂H₈₇N₅O₁₂Si
• 分子量: 1002.37
• InChiKey: MHZKBELZLMHYMX-JACVUXESSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.08
• 重原子数：
  70
• 可旋转键数：
  15
• 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)-18-[(4-methoxyphenyl)methyl]-15,19-dimethyl-3-(2-methylpropyl)-2,5,8,13,17,20-hexaoxo-6,11-di(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 盐酸 作用下， 以 乙酸乙酯 为溶剂， 生成
  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：

  [(2S)-1-[[(2S)-1-[(2S)-2-[[(2S)-3-(4-methoxyphenyl)-1-[(2R,3S)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxo-4-(2-trimethylsilylethoxymethoxy)butan-2-yl]oxy-1-oxopropan-2-yl]-methylcarbamoyl]pyrrolidin-1-yl]-4-methyl-1-oxopentan-2-yl]amino]-3-methyl-1-oxobutan-2-yl] (3S,4R)-5-methyl-4-(phenylmethoxycarbonylamino)-3-tri(propan-2-yl)silyloxyhexanoate 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 、 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 tert-butyl N-[(3S,6S,10S,11R,14S,15R,18S,21S)-18-[(4-methoxyphenyl)methyl]-15,19-dimethyl-3-(2-methylpropyl)-2,5,8,13,17,20-hexaoxo-6,11-di(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：

  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