(2S,3R,4S)-2,3-bis[[tert-butyl(dimethyl)silyl]oxy]-4-methoxyhex-5-enal | 1253795-86-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R,4S)-2,3-bis[[tert-butyl(dimethyl)silyl]oxy]-4-methoxyhex-5-enal
• CAS: 1253795-86-6
• 化学式: C₁₉H₄₀O₄Si₂
• 分子量: 388.695
• InChiKey: BCZTYVGZTXKBLX-GVDBMIGSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.17
• 重原子数：
  25
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3R,4S)-2,3-bis[[tert-butyl(dimethyl)silyl]oxy]-4-methoxyhex-5-enal 、 乙氧甲酰基亚乙基三苯基 以 甲苯 为溶剂， 以87%的产率得到ethyl (4R,5R,6S,E)-4,5-bis((tert-butyldimethylsilyl)oxy)-6-methoxy-2-methylocta-2,7-dienoate
  参考文献：
  名称：

  Synthesis of congeners of migrastatin and dorrigocin A from d-xylose

  摘要：

  Migrastatin and dorrigocin A analogues have potential as anti-metastatic agents that act by targeting the actin-bundling protein, fascin. Syntheses of close structural analogues of these agents have been achieved. Wittig and Ando olefination reactions with an aldehyde obtained from D-xylose, respectively, gave two trisubstituted alkene intermediates that were then elaborated into either macrolactone or macrolactam analogues of migrastatin or to an acyclic dorrigocin A analogue. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.07.141
• 作为产物：
  描述：

  (2R,3R,4S)-2,3-bis[[tert-butyl(dimethyl)silyl]oxy]-4-methoxyhex-5-en-1-ol 在 吡啶 、 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 以89%的产率得到(2S,3R,4S)-2,3-bis[[tert-butyl(dimethyl)silyl]oxy]-4-methoxyhex-5-enal
  参考文献：
  名称：

  Synthesis of congeners of migrastatin and dorrigocin A from d-xylose

  摘要：

  Migrastatin and dorrigocin A analogues have potential as anti-metastatic agents that act by targeting the actin-bundling protein, fascin. Syntheses of close structural analogues of these agents have been achieved. Wittig and Ando olefination reactions with an aldehyde obtained from D-xylose, respectively, gave two trisubstituted alkene intermediates that were then elaborated into either macrolactone or macrolactam analogues of migrastatin or to an acyclic dorrigocin A analogue. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.07.141

文献信息

• Synthesis of congeners of migrastatin and dorrigocin A from d-xylose
  作者：Ying Zhou、Paul V. Murphy

  DOI：10.1016/j.tetlet.2010.07.141

  日期：2010.10

  Migrastatin and dorrigocin A analogues have potential as anti-metastatic agents that act by targeting the actin-bundling protein, fascin. Syntheses of close structural analogues of these agents have been achieved. Wittig and Ando olefination reactions with an aldehyde obtained from D-xylose, respectively, gave two trisubstituted alkene intermediates that were then elaborated into either macrolactone or macrolactam analogues of migrastatin or to an acyclic dorrigocin A analogue. (C) 2010 Elsevier Ltd. All rights reserved.