tert-butyl (2S,3S,4S)-3,4-dihydroxy-2-isobutyl-5-oxo-1-pyrrolidinecarboxylate | 1188511-21-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: tert-butyl (2S,3S,4S)-3,4-dihydroxy-2-isobutyl-5-oxo-1-pyrrolidinecarboxylate
• 英文别名: tert-butyl (2S,3S,4S)-3,4-dihydroxy-2-(2-methylpropyl)-5-oxopyrrolidine-1-carboxylate
• CAS: 1188511-21-8
• 化学式: C₁₃H₂₃NO₅
• 分子量: 273.329
• InChiKey: FFOPRJSNIFJDLY-GUBZILKMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  87.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl (2S,3S,4S)-3,4-dihydroxy-2-isobutyl-5-oxo-1-pyrrolidinecarboxylate 、 2,2-二甲氧基丙烷 在 对甲苯磺酸 作用下， 以 水 为溶剂， 反应 0.83h， 以88%的产率得到tert-butyl (3aS,6S,6aS)-tetrahydro-6-isobutyl-2,2-dimethyl-4-oxo-5H-1,3-dioxolo[4,5-c]pyrrole-5-carboxylate
  参考文献：
  名称：

  Concise Synthesis of PM-94128 and Y-05460M-A

  摘要：

  The enantioselective total synthesis of PM-94128, a potent cytotoxin of microbial origin, was accomplished by a concise nine-step sequence of reactions in 14% overall yield from N-Boc-L-leucine. The synthesis of Y-05460M-A, a one-carbon lower homologue of PM-94128, was also achieved from N-BOC-L-valine by the same approach, which enabled its stereochemical determination.

  DOI：

  10.1021/jo9014968
• 作为产物：
  描述：

  tert-butyl (S)-2,5-dihydro-2-isobutyl-5-oxo-1H-pyrrole-1-carboxylate 在 四氧化锇 、 水 、 N-甲基吗啉氧化物 作用下， 以 丙酮 、 乙腈 为溶剂， 反应 32.0h， 以58%的产率得到tert-butyl (2S,3S,4S)-3,4-dihydroxy-2-isobutyl-5-oxo-1-pyrrolidinecarboxylate
  参考文献：
  名称：

  Concise Synthesis of PM-94128 and Y-05460M-A

  摘要：

  The enantioselective total synthesis of PM-94128, a potent cytotoxin of microbial origin, was accomplished by a concise nine-step sequence of reactions in 14% overall yield from N-Boc-L-leucine. The synthesis of Y-05460M-A, a one-carbon lower homologue of PM-94128, was also achieved from N-BOC-L-valine by the same approach, which enabled its stereochemical determination.

  DOI：

  10.1021/jo9014968

文献信息

• Concise Synthesis of PM-94128 and Y-05460M-A
  作者：Masaru Enomoto、Shigefumi Kuwahara

  DOI：10.1021/jo9014968

  日期：2009.10.2

  The enantioselective total synthesis of PM-94128, a potent cytotoxin of microbial origin, was accomplished by a concise nine-step sequence of reactions in 14% overall yield from N-Boc-L-leucine. The synthesis of Y-05460M-A, a one-carbon lower homologue of PM-94128, was also achieved from N-BOC-L-valine by the same approach, which enabled its stereochemical determination.