2-[(1R,2S,3S,5R)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-(dimethoxymethyl)cyclopentyl]acetaldehyde | 1142204-02-1

• 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: 2-[(1R,2S,3S,5R)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-(dimethoxymethyl)cyclopentyl]acetaldehyde
• CAS: 1142204-02-1
• 化学式: C₂₂H₄₆O₅Si₂
• 分子量: 446.775
• InChiKey: PWCOWJMPYVKNSP-RDGPPVDQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.61
• 重原子数：
  29
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[(1R,2S,3S,5R)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-(dimethoxymethyl)cyclopentyl]acetaldehyde 、 <(3Z)-nonen-1-yl>triphenylphosphonium iodide 在 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 tert-butyl-[(1S,2S,3R,4R)-4-[tert-butyl(dimethyl)silyl]oxy-2-(dimethoxymethyl)-3-[(2Z,5Z)-undeca-2,5-dienyl]cyclopentyl]oxy-dimethylsilane
  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-[(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