allyl N-(((2R,3S,4S,5R)-5-hydroxy-3-((4-methoxybenzyl)oxy)-2,4-dimethyloctanoyl)-L-phenylalanyl)-N-methyl-L-phenylalaninate | 1343505-27-0

• 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: allyl N-(((2R,3S,4S,5R)-5-hydroxy-3-((4-methoxybenzyl)oxy)-2,4-dimethyloctanoyl)-L-phenylalanyl)-N-methyl-L-phenylalaninate
• CAS: 1343505-27-0
• 化学式: C₄₀H₅₂N₂O₇
• 分子量: 672.862
• InChiKey: MSAFIZCZUVACSV-OYYSZJOGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.54
• 重原子数：
  49.0
• 可旋转键数：
  20.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  114.4
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  allyl N-(((2R,3S,4S,5R)-5-hydroxy-3-((4-methoxybenzyl)oxy)-2,4-dimethyloctanoyl)-L-phenylalanyl)-N-methyl-L-phenylalaninate 在 吗啉 、 四(三苯基膦)钯 作用下， 以 四氢呋喃 为溶剂， 以85%的产率得到N-(((2R,3S,4S,5R)-5-hydroxy-3-((4-methoxybenzyl)oxy)-2,4-dimethyloctanoyl)-L-phenylalanyl)-N-methyl-L-phenylalanine
  参考文献：
  名称：

  Synthetic studies of stereocalpin A and its C5-epimer: total synthesis of 11-epi- and 5,11-diepi-stereocalpin A

  摘要：

  This Letter describes the synthetic studies of stereocalpin A and its C5-epimer. After various cyclization attempts, successful macrolactamization at 9-10 position was tried inorder to obtain stereocalpin A and its C5-epimer, which were accompanied by complete racemization and resulted in the synthesis of 11-epi- and 5,11-diepi-stereocalpin A. Highly functionalized octanoic acid motif of the depsipeptide was constructed by applying Paterson's aldol methodology, owing to its diversity in synthesizing various analogs of aliphatic acid. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.08.158
• 作为产物：
  描述：

  在 N-乙基哌啶 、 2,6-二甲基吡啶 、 sodium chlorite 、 sodium dihydrogenphosphate dihydrate 、 2-甲基-2-丁烯 、 二异丁基氢化铝 、 戴斯-马丁氧化剂 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 甲醇 、 二氯甲烷 、 水 、 乙腈 、 叔丁醇 为溶剂， 反应 17.75h， 生成 allyl N-(((2R,3S,4S,5R)-5-hydroxy-3-((4-methoxybenzyl)oxy)-2,4-dimethyloctanoyl)-L-phenylalanyl)-N-methyl-L-phenylalaninate
  参考文献：
  名称：

  Synthetic studies of stereocalpin A and its C5-epimer: total synthesis of 11-epi- and 5,11-diepi-stereocalpin A

  摘要：

  This Letter describes the synthetic studies of stereocalpin A and its C5-epimer. After various cyclization attempts, successful macrolactamization at 9-10 position was tried inorder to obtain stereocalpin A and its C5-epimer, which were accompanied by complete racemization and resulted in the synthesis of 11-epi- and 5,11-diepi-stereocalpin A. Highly functionalized octanoic acid motif of the depsipeptide was constructed by applying Paterson's aldol methodology, owing to its diversity in synthesizing various analogs of aliphatic acid. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.08.158