methyl 2-[(1R,2S,3S,5R)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-(dimethoxymethyl)cyclopentyl]acetate | 1142204-00-9

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: methyl 2-[(1R,2S,3S,5R)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-(dimethoxymethyl)cyclopentyl]acetate
• CAS: 1142204-00-9
• 化学式: C₂₃H₄₈O₆Si₂
• 分子量: 476.802
• InChiKey: LZMHDXLFYOHLNZ-DMUMMCEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.59
• 重原子数：
  31
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 2-[(1R,2S,3S,5R)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-(dimethoxymethyl)cyclopentyl]acetate 在 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 反应 1.0h， 生成 2-[(1R,2S,3S,5R)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-(dimethoxymethyl)cyclopentyl]acetaldehyde
  参考文献：
  名称：

  Total synthesis of 4-F3t-neuroprostane and its 4-epimer

  摘要：

  The first synthesis of 4-F-3t-Neuroprostane 1a and its 4-epimer is described. This molecule presents an important contribution to the study of neuronal oxidative stress in DHA-omega 3 depleted brain. The key step involves the introduction of two unsaturated side chains into the chiral polyfunctional cyclopentane 4 via E selective HWE reaction and Z selective Wittig olefination for alpha and omega chains, respectively. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.01.075
• 作为产物：
  描述：

  methyl 2-[(3S,5R)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-(dimethoxymethyl)cyclopenten-1-yl]acetate 在 吡啶 、 dipotassium diazodicarboxylate salt 作用下， 以 甲醇 、 溶剂黄146 、 丁酮 为溶剂， 反应 72.0h， 以72%的产率得到methyl 2-[(1R,2S,3S,5R)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-(dimethoxymethyl)cyclopentyl]acetate
  参考文献：
  名称：

  Total synthesis of 4-F3t-neuroprostane and its 4-epimer

  摘要：

  The first synthesis of 4-F-3t-Neuroprostane 1a and its 4-epimer is described. This molecule presents an important contribution to the study of neuronal oxidative stress in DHA-omega 3 depleted brain. The key step involves the introduction of two unsaturated side chains into the chiral polyfunctional cyclopentane 4 via E selective HWE reaction and Z selective Wittig olefination for alpha and omega chains, respectively. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.01.075

文献信息

• Total synthesis of 4-F3t-neuroprostane and its 4-epimer
  作者：Anne-Laure Auvinet、Barbara Eignerová、Alexandre Guy、Martin Kotora、Thierry Durand

  DOI：10.1016/j.tetlet.2009.01.075

  日期：2009.4

  The first synthesis of 4-F-3t-Neuroprostane 1a and its 4-epimer is described. This molecule presents an important contribution to the study of neuronal oxidative stress in DHA-omega 3 depleted brain. The key step involves the introduction of two unsaturated side chains into the chiral polyfunctional cyclopentane 4 via E selective HWE reaction and Z selective Wittig olefination for alpha and omega chains, respectively. (C) 2009 Elsevier Ltd. All rights reserved.