dibenzyl (3R,6S,9R,16S,17S,20R,23S)-4,6-dimethyl-3-(2-methylpropyl)-2,5,8,15,19,22-hexaoxo-7-phenylmethoxy-16-(phenylmethoxycarbonylamino)-20-[(1S)-1-phenylmethoxyethyl]-17-propan-2-yl-18-oxa-1,4,7,13,14,21,27-heptazatricyclo[21.4.0.09,14]heptacosane-13,27-dicarboxylate | 439293-00-2

• 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: dibenzyl (3R,6S,9R,16S,17S,20R,23S)-4,6-dimethyl-3-(2-methylpropyl)-2,5,8,15,19,22-hexaoxo-7-phenylmethoxy-16-(phenylmethoxycarbonylamino)-20-[(1S)-1-phenylmethoxyethyl]-17-propan-2-yl-18-oxa-1,4,7,13,14,21,27-heptazatricyclo[21.4.0.09,14]heptacosane-13,27-dicarboxylate
• CAS: 439293-00-2
• 化学式: C₆₈H₈₂N₈O₁₅
• 分子量: 1251.44
• InChiKey: GMVALDNTMXNGMS-HQHRVAGFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.7
• 重原子数：
  91
• 可旋转键数：
  20
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  253
• 氢给体数：
  2
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  dibenzyl (3R,6S,9R,16S,17S,20R,23S)-4,6-dimethyl-3-(2-methylpropyl)-2,5,8,15,19,22-hexaoxo-7-phenylmethoxy-16-(phenylmethoxycarbonylamino)-20-[(1S)-1-phenylmethoxyethyl]-17-propan-2-yl-18-oxa-1,4,7,13,14,21,27-heptazatricyclo[21.4.0.09,14]heptacosane-13,27-dicarboxylate 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 16.0h， 以100%的产率得到(3R,6S,9R,16S,17S,20R,23S)-16-Amino-7-hydroxy-20-((S)-1-hydroxy-ethyl)-3-isobutyl-17-isopropyl-4,6-dimethyl-18-oxa-1,4,7,13,14,21,27-heptaaza-tricyclo[21.4.0.0^9,14]heptacosane-2,5,8,15,19,22-hexaone; hydrochloride
  参考文献：
  名称：

  Synthetic Route to the GE3 Cyclodepsipeptide

  摘要：

  [GRAPHICS]A reasonably efficient [2 + 2 + 2] fragment condensation strategy has been developed for assembling the cyclodepsipeptide sector of GE3 that involves 5-7. A Carpino HATU-mediated macrolactamization was used to close the 19-membered cyclodepsipeptide ring.

  DOI：

  10.1021/ol025895u
• 作为产物：
  描述：

  [(2R,3S)-1-[(2S,3S)-1-[(6R)-6-[[(2S)-1-[[(2R)-1-[(6S)-6-carboxy-2-phenylmethoxycarbonyldiazinan-1-yl]-4-methyl-1-oxopentan-2-yl]-methylamino]-1-oxopropan-2-yl]-phenylmethoxycarbamoyl]-2-phenylmethoxycarbonyldiazinan-1-yl]-4-methyl-1-oxo-2-(2,2,2-trichloroethoxycarbonylamino)pentan-3-yl]oxy-1-oxo-3-phenylmethoxybutan-2-yl]azanium;bromide 在 N-乙基马来酰亚胺 、 碳酸氢钠 、 溶剂黄146 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 、 锌 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 69.42h， 生成 dibenzyl (3R,6S,9R,16S,17S,20R,23S)-4,6-dimethyl-3-(2-methylpropyl)-2,5,8,15,19,22-hexaoxo-7-phenylmethoxy-16-(phenylmethoxycarbonylamino)-20-[(1S)-1-phenylmethoxyethyl]-17-propan-2-yl-18-oxa-1,4,7,13,14,21,27-heptazatricyclo[21.4.0.09,14]heptacosane-13,27-dicarboxylate
  参考文献：
  名称：

  Synthetic Route to the GE3 Cyclodepsipeptide

  摘要：

  [GRAPHICS]A reasonably efficient [2 + 2 + 2] fragment condensation strategy has been developed for assembling the cyclodepsipeptide sector of GE3 that involves 5-7. A Carpino HATU-mediated macrolactamization was used to close the 19-membered cyclodepsipeptide ring.

  DOI：

  10.1021/ol025895u