tert-butyl N-[(1S)-1-[(4S,5S)-5-[[(1S)-1-[(3S)-8-methoxy-1-oxo-3,4-dihydroisochromen-3-yl]-3-methylbutyl]carbamoyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-3-methylbutyl]carbamate | 1188511-24-1

• 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: tert-butyl N-[(1S)-1-[(4S,5S)-5-[[(1S)-1-[(3S)-8-methoxy-1-oxo-3,4-dihydroisochromen-3-yl]-3-methylbutyl]carbamoyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-3-methylbutyl]carbamate
• CAS: 1188511-24-1
• 化学式: C₃₁H₄₈N₂O₈
• 分子量: 576.731
• InChiKey: LBVZJGLEPWIXGG-QAXGJQJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  41
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  121
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[(1S)-1-[(4S,5S)-5-[[(1S)-1-[(3S)-8-methoxy-1-oxo-3,4-dihydroisochromen-3-yl]-3-methylbutyl]carbamoyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-3-methylbutyl]carbamate 在 三溴化硼 、 碳酸氢钠 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 4.0h， 以67%的产率得到4-amino-2,3-dihydroxy-6-methylheptanoic acid [1-(8-hydroxy-1-oxoisochroman-3-yl)-3-methylbutyl]amide
  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：

  (4S,5S)-5-[(1S)-1-tert-butoxycarbonylamino-3-methylbutyl]-2,2-dimethyl-1,3-dioxolane-4-carboxylic acid 、 (1S,3'S)-<1-(3,4-Dihydro-8-methoxy-1-oxo-1H-2-benzopyran-3-yl)-3-methylbutyl>ammonium chloride 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 以32.7 mg的产率得到tert-butyl N-[(1S)-1-[(4S,5S)-5-[[(1S)-1-[(3S)-8-methoxy-1-oxo-3,4-dihydroisochromen-3-yl]-3-methylbutyl]carbamoyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-3-methylbutyl]carbamate
  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.