methyl (1S,2R,3S,4R,5S)-2,4-dibenzyloxy-3-hydroxy-5-nitrocyclopentanecarboxylate | 1137111-80-8

• 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 (1S,2R,3S,4R,5S)-2,4-dibenzyloxy-3-hydroxy-5-nitrocyclopentanecarboxylate
• 英文别名: methyl (1S,2S,3R,4S,5R)-4-hydroxy-2-nitro-3,5-bis(phenylmethoxy)cyclopentane-1-carboxylate
• CAS: 1137111-80-8
• 化学式: C₂₁H₂₃NO₇
• 分子量: 401.416
• InChiKey: DFGYFDQLARNRLS-WKWVNEEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl (1S,2R,3S,4R,5S)-2,4-dibenzyloxy-3-hydroxy-5-nitrocyclopentanecarboxylate 在 palladium 10% on activated carbon 、 氢气 、 柠檬酸 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 50.0h， 以0.16 g的产率得到methyl (1S,2S,3R,4S,5R)-2-amino-3,4,5-trihydroxycyclopentanecarboxylate
  参考文献：
  名称：

  Stereocontrolled transformation of nitrohexofuranoses into cyclopentylamines via 2-oxabicyclo[2.2.1]heptanes. III: synthesis of enantiopure methyl (1S,2S,3R,4S,5R)-2-amino-3,4,5-trihydroxycyclopentanecarboxylate

  摘要：

  The first total synthesis of enantiopure methyl (1S,2S,3R,4S,5R)-2-amino-3,4,5-trihydroxycyclopentanecarboxylate was carried out according to our recent novel strategy for the transformation of nitrohexofuranoses into cyclopentylamines, which is based on in intramolecular cyclization leading to 2-oxabicyclo[2.2.1] heptane derivatives. Differences in reactivity for this key step were rationalized by using molecular mechanism-based calculations. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.12.017
• 作为产物：
  描述：

  (1S,2R,3S,4R,5S)-2,4-dibenzyloxy-3-hydroxy-5-nitrocyclopentanecarboxylic acid 、 三甲基硅烷化重氮甲烷 以 甲醇 、 乙醚 为溶剂， 反应 0.25h， 以0.35 g的产率得到methyl (1S,2R,3S,4R,5S)-2,4-dibenzyloxy-3-hydroxy-5-nitrocyclopentanecarboxylate
  参考文献：
  名称：

  Stereocontrolled transformation of nitrohexofuranoses into cyclopentylamines via 2-oxabicyclo[2.2.1]heptanes. III: synthesis of enantiopure methyl (1S,2S,3R,4S,5R)-2-amino-3,4,5-trihydroxycyclopentanecarboxylate

  摘要：

  The first total synthesis of enantiopure methyl (1S,2S,3R,4S,5R)-2-amino-3,4,5-trihydroxycyclopentanecarboxylate was carried out according to our recent novel strategy for the transformation of nitrohexofuranoses into cyclopentylamines, which is based on in intramolecular cyclization leading to 2-oxabicyclo[2.2.1] heptane derivatives. Differences in reactivity for this key step were rationalized by using molecular mechanism-based calculations. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.12.017