methyl (2S,3R)-2-(2-(2,5-bis(benzyloxy)-3-methoxy-4-methyl-6-nitrophenyl)acetyl)-3-((methylsulfonyloxy)methyl)aziridine-1-carboxylate | 1175522-96-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl (2S,3R)-2-(2-(2,5-bis(benzyloxy)-3-methoxy-4-methyl-6-nitrophenyl)acetyl)-3-((methylsulfonyloxy)methyl)aziridine-1-carboxylate
• CAS: 1175522-96-9
• 化学式: C₃₀H₃₂N₂O₁₁S
• 分子量: 628.657
• InChiKey: ASKWAOAEDLFJMR-MSYZFFFDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.98
• 重原子数：
  44.0
• 可旋转键数：
  14.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  160.58
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  methyl (2S,3R)-2-(2-(2,5-bis(benzyloxy)-3-methoxy-4-methyl-6-nitrophenyl)acetyl)-3-((methylsulfonyloxy)methyl)aziridine-1-carboxylate 在 sodium tetrahydroborate 、 cerium(III) chloride 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.5h， 以93%的产率得到methyl (2S,3R)-2-((R)-2-(2,5-bis(benzyloxy)-3-methoxy-4-methyl-6-nitrophenyl)hydroxyethyl)-3-((methylsulfonyloxy)methyl)aziridine-1-carboxylate
  参考文献：
  名称：

  Synthetic studies toward the mitomycins: construction of the tetracyclic core via a reductive aminocyclization reaction

  摘要：

  The tetracyclic core of the mitomycin family of natural products has been formed in one step from an acyclic precursor via a reductive aminocyclization reaction. Additionally, the eight-membered benzazocine can be prepared without the need for prior activation of the aniline. Construction of a mitomycin K analogue lacking the C9a methoxy moiety is also reported herein. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.05.004
• 作为产物：
  描述：

  methyl (2S,3R)-2-(2-(2,5-bis(benzyloxy)-3-methoxy-4-methyl-6-nitrophenyl)acetyl)-3-(hydroxymethyl)aziridine-1-carboxylate 、 甲基磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以53%的产率得到methyl (2S,3R)-2-(2-(2,5-bis(benzyloxy)-3-methoxy-4-methyl-6-nitrophenyl)acetyl)-3-((methylsulfonyloxy)methyl)aziridine-1-carboxylate
  参考文献：
  名称：

  Synthetic studies toward the mitomycins: construction of the tetracyclic core via a reductive aminocyclization reaction

  摘要：

  The tetracyclic core of the mitomycin family of natural products has been formed in one step from an acyclic precursor via a reductive aminocyclization reaction. Additionally, the eight-membered benzazocine can be prepared without the need for prior activation of the aniline. Construction of a mitomycin K analogue lacking the C9a methoxy moiety is also reported herein. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.05.004