methyl (2S,3R)-2-(2-(2,5-bis(benzyloxy)-3-methoxy-4-methyl-6-nitrophenyl)-1-hydroxyethyl)-3-((4-methoxybenzyloxy)methyl)aziridine-1-carboxylate | 1175522-90-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: methyl (2S,3R)-2-(2-(2,5-bis(benzyloxy)-3-methoxy-4-methyl-6-nitrophenyl)-1-hydroxyethyl)-3-((4-methoxybenzyloxy)methyl)aziridine-1-carboxylate
• CAS: 1175522-90-3
• 化学式: C₃₇H₄₀N₂O₁₀
• 分子量: 672.732
• InChiKey: JKESKJJLMCBRQM-IOEMYKNMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.02
• 重原子数：
  49.0
• 可旋转键数：
  16.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  138.83
• 氢给体数：
  1.0
• 氢受体数：
  10.0

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)-1-hydroxyethyl)-3-((4-methoxybenzyloxy)methyl)aziridine-1-carboxylate 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以98%的产率得到methyl (2S,3R)-2-(2-(2,5-bis(benzyloxy)-3-methoxy-4-methyl-6-nitrophenyl)acetyl)-3-((4-methoxybenzyloxy)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：

  2-methoxy-3,6-dimethyl-5-nitrohydroquinone dibenzyl ether 、 (2S-cis)-methyl ester 2-formyl-3-[(4-methoxyphenyl)methoxymethyl]-1-aziridinecarboxylic acid 在 zinc(II) chloride 、 sodium hexamethyldisilazane 、 水 、 氯化铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以85%的产率得到methyl (2S,3R)-2-(2-(2,5-bis(benzyloxy)-3-methoxy-4-methyl-6-nitrophenyl)-1-hydroxyethyl)-3-((4-methoxybenzyloxy)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