(2S,4E,6R,8E)-2,6-bis(tert-butyldimethylsilyloxy)-9-phenylnona-4,8-dienenitrile | 1254331-91-3

• 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: (2S,4E,6R,8E)-2,6-bis(tert-butyldimethylsilyloxy)-9-phenylnona-4,8-dienenitrile
• 英文别名: (2S,4E,6R,8E)-2,6-di(tert-butyldimethylsilyloxy)-9-phenylnona-4,8-dienenitrile；(2S,4E,6R,8E)-2,6-bis[[tert-butyl(dimethyl)silyl]oxy]-9-phenylnona-4,8-dienenitrile
• CAS: 1254331-91-3
• 化学式: C₂₇H₄₅NO₂Si₂
• 分子量: 471.831
• InChiKey: QRWLGIGQPSGYKK-CPAWVWROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.34
• 重原子数：
  32
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  42.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (2R,4E)-2-tert-butyldimethylsilyloxy-5-phenylpent-4-enal 、 (S)-2-(tert-butyldimethylsilyloxy)-4-(1-phenyl-1H-tetrazol-5-ylsulfonyl)butanenitrile 在 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 为溶剂， 反应 3.75h， 以96%的产率得到(2S,4E,6R,8E)-2,6-bis(tert-butyldimethylsilyloxy)-9-phenylnona-4,8-dienenitrile
  参考文献：
  名称：

  Versatile Configuration-Encoded Strategy for Rapid Synthesis of 1,5-Polyol Stereoisomers

  摘要：

  The isolated stereogenic centers of 1,5-polyol-containing natural products present challenges to synthesis and structure determination. To address this problem, a configuration-encoded strategy defines each configuration within a simple 4-(arylsulfonyl)butyronitrile building block, a repeat unit that is reliably and efficiently coupled in iterative fashion to afford 1,5-polyols of defined stereochemistry. For example, the C27-C40 subunit of tetrafibricin is prepared in five steps and 42% yield. This strategy is amenable to rapid and unambiguous preparation of all configurational permutations of 1,5-polyols with equal facility.

  DOI：

  10.1021/ol1021417

文献信息

• Versatile Configuration-Encoded Strategy for Rapid Synthesis of 1,5-Polyol Stereoisomers
  作者：Gregory K. Friestad、Gopeekrishnan Sreenilayam

  DOI：10.1021/ol1021417

  日期：2010.11.5

  The isolated stereogenic centers of 1,5-polyol-containing natural products present challenges to synthesis and structure determination. To address this problem, a configuration-encoded strategy defines each configuration within a simple 4-(arylsulfonyl)butyronitrile building block, a repeat unit that is reliably and efficiently coupled in iterative fashion to afford 1,5-polyols of defined stereochemistry. For example, the C27-C40 subunit of tetrafibricin is prepared in five steps and 42% yield. This strategy is amenable to rapid and unambiguous preparation of all configurational permutations of 1,5-polyols with equal facility.