(-)-(Z)-(2S,R_S)-4-(p-tolylsulfinyl)-3-buten-2-ol tert-butyldiphenylsilyl ether | 561319-69-5

• 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: (-)-(Z)-(2S,R_S)-4-(p-tolylsulfinyl)-3-buten-2-ol tert-butyldiphenylsilyl ether
• 英文别名: tert-butyl-[(Z,2S)-4-[(R)-(4-methylphenyl)sulfinyl]but-3-en-2-yl]oxy-diphenylsilane
• CAS: 561319-69-5
• 化学式: C₂₇H₃₂O₂SSi
• 分子量: 448.701
• InChiKey: WVHKUQOVVUEJEK-UHNNEXACSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.58
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  45.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (-)-(Z)-(2S,R_S)-4-(p-tolylsulfinyl)-3-buten-2-ol tert-butyldiphenylsilyl ether 在 叔丁基过氧化氢 、 正丁基锂 、 4 A molecular sieve 、 magnesium monoperoxyphthalate hexahydrate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 28.5h， 生成 (-)-(2S,3R,1'S)-3-(1'-tert-butyldiphenylsilyloxyethyl)-2-(p-tolylsulfonyl)oxirane
  参考文献：
  名称：

  Nucleophilic Epoxidation of γ-Hydroxyvinyl Sulfoxide Derivatives

  摘要：

  The nucleophilic epoxidation of simple (gamma-silyloxy)vinyl sulfoxides takes place with complete stereocontrol and high yields. For substrates bearing an additional substituent at the gamma position, a reinforcing/nonreinforcing scenario is operative. While E and Z silylated substrates undergo a primarily sulfur directed epoxidation with good to excellent diastereocontrol, the related (E)-(2-methoxyethoxy)methyl ethers display diminished selectivity for the diastereomer derived from the nonreinforcing scenario.

  DOI：

  10.1021/jo0342828
• 作为产物：
  描述：

  (R)-(+)-对甲苯亚磺酸D-甲酯 、 (S)-2-(叔丁基二苯基硅氧基)丙醛 、 甲基膦酸二甲酯 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 1.17h， 以36%的产率得到(-)-(Z)-(2S,R_S)-4-(p-tolylsulfinyl)-3-buten-2-ol tert-butyldiphenylsilyl ether
  参考文献：
  名称：

  Nucleophilic Epoxidation of γ-Hydroxyvinyl Sulfoxide Derivatives

  摘要：

  The nucleophilic epoxidation of simple (gamma-silyloxy)vinyl sulfoxides takes place with complete stereocontrol and high yields. For substrates bearing an additional substituent at the gamma position, a reinforcing/nonreinforcing scenario is operative. While E and Z silylated substrates undergo a primarily sulfur directed epoxidation with good to excellent diastereocontrol, the related (E)-(2-methoxyethoxy)methyl ethers display diminished selectivity for the diastereomer derived from the nonreinforcing scenario.

  DOI：

  10.1021/jo0342828

文献信息

• Nucleophilic Epoxidation of γ-Hydroxyvinyl Sulfoxide Derivatives
  作者：Roberto Fernández de la Pradilla、María Victoria Buergo、Pilar Manzano、Carlos Montero、Julián Priego、Alma Viso、Félix H. Cano、María Paz Martínez-Alcázar

  DOI：10.1021/jo0342828

  日期：2003.6.1

  The nucleophilic epoxidation of simple (gamma-silyloxy)vinyl sulfoxides takes place with complete stereocontrol and high yields. For substrates bearing an additional substituent at the gamma position, a reinforcing/nonreinforcing scenario is operative. While E and Z silylated substrates undergo a primarily sulfur directed epoxidation with good to excellent diastereocontrol, the related (E)-(2-methoxyethoxy)methyl ethers display diminished selectivity for the diastereomer derived from the nonreinforcing scenario.