trimethyl-[(Z)-3-[(2R,3R,4S,5R,6R)-2,4,5-trimethoxy-6-(methoxymethyl)oxan-3-yl]oxyprop-1-enyl]silane | 951004-87-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: trimethyl-[(Z)-3-[(2R,3R,4S,5R,6R)-2,4,5-trimethoxy-6-(methoxymethyl)oxan-3-yl]oxyprop-1-enyl]silane
• CAS: 951004-87-8
• 化学式: C₁₆H₃₂O₆Si
• 分子量: 348.512
• InChiKey: HZPYSBBCZDFBDK-GLEBBMLVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.85
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  trimethyl-[(Z)-3-[(2R,3R,4S,5R,6R)-2,4,5-trimethoxy-6-(methoxymethyl)oxan-3-yl]oxyprop-1-enyl]silane 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以75%的产率得到(2R,3R,4S,4aS,8aR)-3,4-dimethoxy-2-(methoxymethyl)-2,3,4,4a,6,8a-hexahydropyrano[3,2-b]pyran
  参考文献：
  名称：

  Intramolecular Vinylsilane−Oxocarbenium Condensations:  Concise Assembly of Cis-Bicyclic Ether Arrays

  摘要：

  Lewis acid-mediated intramolecular attack of vinylsilanes at tethered oxonium precursors 1 results in a rapid assembly of the cis-fused bicyclic ether species 3, with complete regio- and stereospecific control, and in some cases near-quantitative yield. Continued investigation suggests a general approach to a variety of such ether frameworks.

  DOI：

  10.1021/ol071349v
• 作为产物：
  描述：

  3,4,6-三-O-甲基-D-葡萄糖醛 在 sodium hydride 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 为溶剂， 生成 trimethyl-[(Z)-3-[(2R,3R,4S,5R,6R)-2,4,5-trimethoxy-6-(methoxymethyl)oxan-3-yl]oxyprop-1-enyl]silane
  参考文献：
  名称：

  Intramolecular Vinylsilane−Oxocarbenium Condensations:  Concise Assembly of Cis-Bicyclic Ether Arrays

  摘要：

  Lewis acid-mediated intramolecular attack of vinylsilanes at tethered oxonium precursors 1 results in a rapid assembly of the cis-fused bicyclic ether species 3, with complete regio- and stereospecific control, and in some cases near-quantitative yield. Continued investigation suggests a general approach to a variety of such ether frameworks.

  DOI：

  10.1021/ol071349v

文献信息

• Intramolecular Vinylsilane−Oxocarbenium Condensations:  Concise Assembly of Cis-Bicyclic Ether Arrays
  作者：Stephen Philip Fearnley、Pedro Lory

  DOI：10.1021/ol071349v

  日期：2007.8.1

  Lewis acid-mediated intramolecular attack of vinylsilanes at tethered oxonium precursors 1 results in a rapid assembly of the cis-fused bicyclic ether species 3, with complete regio- and stereospecific control, and in some cases near-quantitative yield. Continued investigation suggests a general approach to a variety of such ether frameworks.