S-((7R)-7-((tert-butyldimethylsilyl)oxy)-1-((3S,9S,14aR)-9-(cyclohexylmethyl)-6,6-dimethyl-1,4,7,10-tetraoxotetradecahydropyrrolo[1,2-a][1,4,7,10]tetraazacyclododecin-3-yl)-6-oxooctan-3-yl) O-ethyl carbonodithioate | 1445578-74-4

• 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: S-((7R)-7-((tert-butyldimethylsilyl)oxy)-1-((3S,9S,14aR)-9-(cyclohexylmethyl)-6,6-dimethyl-1,4,7,10-tetraoxotetradecahydropyrrolo[1,2-a][1,4,7,10]tetraazacyclododecin-3-yl)-6-oxooctan-3-yl) O-ethyl carbonodithioate
• CAS: 1445578-74-4
• 化学式: C₃₇H₆₄N₄O₇S₂Si
• 分子量: 769.155
• InChiKey: ZTWISVPOBFAALY-UMHADGDUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.79
• 重原子数：
  51.0
• 可旋转键数：
  13.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  143.14
• 氢给体数：
  3.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  S-((7R)-7-((tert-butyldimethylsilyl)oxy)-1-((3S,9S,14aR)-9-(cyclohexylmethyl)-6,6-dimethyl-1,4,7,10-tetraoxotetradecahydropyrrolo[1,2-a][1,4,7,10]tetraazacyclododecin-3-yl)-6-oxooctan-3-yl) O-ethyl carbonodithioate 在 过氧化双月桂酰 作用下， 以 异丙醇 为溶剂， 反应 5.0h， 以62%的产率得到(3S,9S,14aR)-3-((R)-7-((tert-butyldimethylsilyl)oxy)-6-oxooctyl)-9-(cyclohexylmethyl)-6,6-dimethyldecahydropyrrolo[1,2-a][1,4,7,10]tetraazacyclododecine-1,4,7,10-tetraone
  参考文献：
  名称：

  Flexible Synthesis and Evaluation of Diverse Anti-Apicomplexa Cyclic Peptides

  摘要：

  A modular approach to synthesize anti-Apicomplexa parasite inhibitors was developed that takes advantage of a pluripotent cyclic tetrapeptide scaffold capable of adjusting appendage and skeletal diversities in only a few steps (one to three steps). The diversification processes make use of selective radical coupling reactions and involve a new example of a reductive carbon nitrogen cleavage reaction with SmI2. The resulting bioactive cyclic peptides have revealed new insights into structural factors that govern selectivity between Apicomplexa parasites such as Toxoplasma and Plasmodium and human cells.

  DOI：

  10.1021/jo4001492
• 作为产物：
  描述：

  (R)-1-chloro-3-(tert-butyldimethylsilyloxy)butan-2-one 以 1,2-二氯乙烷 、 丙酮 为溶剂， 反应 4.5h， 生成 S-((7R)-7-((tert-butyldimethylsilyl)oxy)-1-((3S,9S,14aR)-9-(cyclohexylmethyl)-6,6-dimethyl-1,4,7,10-tetraoxotetradecahydropyrrolo[1,2-a][1,4,7,10]tetraazacyclododecin-3-yl)-6-oxooctan-3-yl) O-ethyl carbonodithioate
  参考文献：
  名称：

  Flexible Synthesis and Evaluation of Diverse Anti-Apicomplexa Cyclic Peptides

  摘要：

  A modular approach to synthesize anti-Apicomplexa parasite inhibitors was developed that takes advantage of a pluripotent cyclic tetrapeptide scaffold capable of adjusting appendage and skeletal diversities in only a few steps (one to three steps). The diversification processes make use of selective radical coupling reactions and involve a new example of a reductive carbon nitrogen cleavage reaction with SmI2. The resulting bioactive cyclic peptides have revealed new insights into structural factors that govern selectivity between Apicomplexa parasites such as Toxoplasma and Plasmodium and human cells.

  DOI：

  10.1021/jo4001492