(2S,6S)-2-[(2S)-4-chloro-2-hydroxybutoxy]-6-[(2S)-1-tri(propan-2-yl)silyloxypropan-2-yl]oxane-2-carbonitrile | 929083-81-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,6S)-2-[(2S)-4-chloro-2-hydroxybutoxy]-6-[(2S)-1-tri(propan-2-yl)silyloxypropan-2-yl]oxane-2-carbonitrile
• CAS: 929083-81-8
• 化学式: C₂₂H₄₂ClNO₄Si
• 分子量: 448.118
• InChiKey: YMLMEBOKNLDZLU-CMOCDZPBSA-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：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  71.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,6S)-2-[(2S)-4-chloro-2-hydroxybutoxy]-6-[(2S)-1-tri(propan-2-yl)silyloxypropan-2-yl]oxane-2-carbonitrile 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以72%的产率得到
  参考文献：
  名称：

  Diastereoselective Synthesis of the Pectenotoxin 2 Non-Anomeric AB Spiroacetal

  摘要：

  The reductive cyclization reaction of a cyanoacetal has been used to prepare the pectenotoxin 2 (PTX-2) AB spiroacetal with high diastereoselectively for the first time. The strategy is convergent and makes use of the axial-selective reductive lithiation of 2-cyano tetrahydropyran rings to introduce the spiroacetal center with the desired non-anomeric selectivity.

  DOI：

  10.1021/ol0630447
• 作为产物：
  描述：

  {2-[2-(2-chloro-ethyl)-1,4,6-trioxa-spiro[4.5]dec-7-yl]-propoxy}-triisopropyl-silane 、 三甲基氰硅烷 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以50%的产率得到2-(3-chloro-1-hydroxymethyl-propoxy)-6-(1-methyl-2-triisopropylsilanyloxy-ethyl)-tetrahydro-pyran-2-carbonitrile
  参考文献：
  名称：

  Diastereoselective Synthesis of the Pectenotoxin 2 Non-Anomeric AB Spiroacetal

  摘要：

  The reductive cyclization reaction of a cyanoacetal has been used to prepare the pectenotoxin 2 (PTX-2) AB spiroacetal with high diastereoselectively for the first time. The strategy is convergent and makes use of the axial-selective reductive lithiation of 2-cyano tetrahydropyran rings to introduce the spiroacetal center with the desired non-anomeric selectivity.

  DOI：

  10.1021/ol0630447

文献信息

• Diastereoselective Synthesis of the Pectenotoxin 2 Non-Anomeric AB Spiroacetal
  作者：Danielle Vellucci、Scott D. Rychnovsky

  DOI：10.1021/ol0630447

  日期：2007.2.1

  The reductive cyclization reaction of a cyanoacetal has been used to prepare the pectenotoxin 2 (PTX-2) AB spiroacetal with high diastereoselectively for the first time. The strategy is convergent and makes use of the axial-selective reductive lithiation of 2-cyano tetrahydropyran rings to introduce the spiroacetal center with the desired non-anomeric selectivity.