dibenzyl (3R,6S,9R,16S,17S,20R,23S)-6-(methoxymethyl)-3,4-dimethyl-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 | 1104899-87-7

• 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: dibenzyl (3R,6S,9R,16S,17S,20R,23S)-6-(methoxymethyl)-3,4-dimethyl-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: 1104899-87-7
• 化学式: C₆₆H₇₈N₈O₁₆
• 分子量: 1239.39
• InChiKey: STJFPENIWMVDJN-BEIAOYMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  90
• 可旋转键数：
  20
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  262
• 氢给体数：
  2
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  dibenzyl (3R,6S,9R,16S,17S,20R,23S)-6-(methoxymethyl)-3,4-dimethyl-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 盐酸 、 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 24.0h， 生成 (3R,6S,9R,16S,17S,20R,23S)-16-amino-7-hydroxy-20-[(1S)-1-hydroxyethyl]-6-(methoxymethyl)-3,4-dimethyl-17-propan-2-yl-18-oxa-1,4,7,13,14,21,27-heptazatricyclo[21.4.0.09,14]heptacosane-2,5,8,15,19,22-hexone;hydrochloride
  参考文献：
  名称：

  Total Synthesis of (+)-Azinothricin and (+)-Kettapeptin

  摘要：

  Asymmetric total syntheses of (+)-azinothricin and (+)-kettapeptin have been completed through a common new pathway that exploits a highly chemoselective coupling reaction between the fully elaborated cyclodepsipeptide 5 and the glycal activated esters 3 and 4 at the final stages of both respective syntheses.

  DOI：

  10.1021/ol802817t
• 作为产物：
  描述：

  、 氯甲酸苄酯 在 碳酸氢钠 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 2.0h， 以0.84 g的产率得到dibenzyl (3R,6S,9R,16S,17S,20R,23S)-6-(methoxymethyl)-3,4-dimethyl-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：

  Total Synthesis of (+)-Azinothricin and (+)-Kettapeptin

  摘要：

  Asymmetric total syntheses of (+)-azinothricin and (+)-kettapeptin have been completed through a common new pathway that exploits a highly chemoselective coupling reaction between the fully elaborated cyclodepsipeptide 5 and the glycal activated esters 3 and 4 at the final stages of both respective syntheses.

  DOI：

  10.1021/ol802817t