(Z)-(2R,3R,4S)-2,3,4-Trimethoxy-6-trimethylsilanyl-hex-5-enal | 135456-80-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Z)-(2R,3R,4S)-2,3,4-Trimethoxy-6-trimethylsilanyl-hex-5-enal
• 英文别名: (Z,2R,3R,4S)-2,3,4-trimethoxy-6-trimethylsilylhex-5-enal
• CAS: 135456-80-3
• 化学式: C₁₂H₂₄O₄Si
• 分子量: 260.406
• InChiKey: VTIHMNJGOCNUQK-WEJZEEGASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.66
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  (Z)-(2R,3R,4S)-2,3,4-Trimethoxy-6-trimethylsilanyl-hex-5-enal 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 24.25h， 生成 4-Methyl-N-((1R,4S,5R,6S)-4,5,6-trimethoxy-cyclohex-2-enyl)-benzenesulfonamide
  参考文献：
  名称：

  An approach to total synthesis of (+)-lycoricidine

  摘要：

  A convergent synthesis of a protected version of (+)-lycoricidine has been accomplished in 13 steps from L-arabinose. Preparation of the aminocyclitol moiety 50 employed a novel vinylsilane-terminated N-sulfonyliminium ion cyclization of vinylsilane aldehyde 42. Closure of the B-ring using an intramolecular Heck reaction afforded lycoricidine derivative 58. An unexpected cyclization of vinylsilane aldehyde 42 allowed for the stereodivergent preparation of semiprotected conduritols 43 and 45.

  DOI：

  10.1021/jo00070a016
• 作为产物：
  描述：

  (Z)-(2S,3R,4S)-2,3,4-Trimethoxy-6-trimethylsilanyl-hex-5-en-1-ol 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 生成 (Z)-(2R,3R,4S)-2,3,4-Trimethoxy-6-trimethylsilanyl-hex-5-enal
  参考文献：
  名称：

  A strategy for synthesis of conduritols and related cyclitols via stereodivergent vinylsilane-aldehyde cyclizations

  摘要：

  A novel stereospecific and stereodivergent cyclization of vinylsilane-aldehyde 10, derived from L-arabinose, has been used to prepare the scalemic protected conduritols 11 and 12.

  DOI：

  10.1021/jo00017a005

文献信息

• Weinreb, Steven M., Bulletin des Societes Chimiques Belges, 1992, vol. 101, # 5, p. 381 - 392
  作者：Weinreb, Steven M.

  DOI：——

  日期：——
• A strategy for synthesis of conduritols and related cyclitols via stereodivergent vinylsilane-aldehyde cyclizations
  作者：Matthias C. McIntosh、Steven M. Weinreb

  DOI：10.1021/jo00017a005

  日期：1991.8

  A novel stereospecific and stereodivergent cyclization of vinylsilane-aldehyde 10, derived from L-arabinose, has been used to prepare the scalemic protected conduritols 11 and 12.
• An approach to total synthesis of (+)-lycoricidine
  作者：Matthias C. McIntosh、Steven M. Weinreb

  DOI：10.1021/jo00070a016

  日期：1993.8

  A convergent synthesis of a protected version of (+)-lycoricidine has been accomplished in 13 steps from L-arabinose. Preparation of the aminocyclitol moiety 50 employed a novel vinylsilane-terminated N-sulfonyliminium ion cyclization of vinylsilane aldehyde 42. Closure of the B-ring using an intramolecular Heck reaction afforded lycoricidine derivative 58. An unexpected cyclization of vinylsilane aldehyde 42 allowed for the stereodivergent preparation of semiprotected conduritols 43 and 45.