1,2-dideoxy-5,6-(1-methylethylidene)-3-O-(triethylsilyl)-D-arabino-hex-1-enitol 4-(prop-2-enoate) | 1357379-97-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2-dideoxy-5,6-(1-methylethylidene)-3-O-(triethylsilyl)-D-arabino-hex-1-enitol 4-(prop-2-enoate)
• 英文别名: 1-(2,2-dimethyl-1,3-dioxolan-4-yl)-2-[(triethylsilyl)oxy]but-3-en-1-yl prop-2-enoate；[(1R,2R)-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-triethylsilyloxybut-3-enyl] prop-2-enoate
• CAS: 1357379-97-5
• 化学式: C₁₈H₃₂O₅Si
• 分子量: 356.535
• InChiKey: VDDDHGDYFHVVNB-INMHGKMJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.81
• 重原子数：
  24
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,2-dideoxy-5,6-(1-methylethylidene)-3-O-(triethylsilyl)-D-arabino-hex-1-enitol 4-(prop-2-enoate) 在 吡啶 、 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 (-)-cleistenolide
  参考文献：
  名称：

  Total Synthesis of (−)-Cleistenolide

  摘要：

  AbstractAn efficient and short total synthesis of (−)‐cleistenolide (1) from D‐mannitol with an overall yield of 23.6% is described. The chiron approach for the synthesis of (−)‐cleistenolide involves a one‐C‐atom Wittig olefination, a selective allylic triethylsilyl protection, and a Grubbs‐catalyzed ring‐closure‐metathesis (RCM) reaction as the key steps.

  DOI：

  10.1002/hlca.201100086
• 作为产物：
  描述：

  (1S,2R)-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-butene-1,2-diol 在 咪唑 、 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.08h， 生成 1,2-dideoxy-5,6-(1-methylethylidene)-3-O-(triethylsilyl)-D-arabino-hex-1-enitol 4-(prop-2-enoate)
  参考文献：
  名称：

  Total Synthesis of (−)-Cleistenolide

  摘要：

  AbstractAn efficient and short total synthesis of (−)‐cleistenolide (1) from D‐mannitol with an overall yield of 23.6% is described. The chiron approach for the synthesis of (−)‐cleistenolide involves a one‐C‐atom Wittig olefination, a selective allylic triethylsilyl protection, and a Grubbs‐catalyzed ring‐closure‐metathesis (RCM) reaction as the key steps.

  DOI：

  10.1002/hlca.201100086

文献信息

• Total Synthesis of (−)-Cleistenolide
  作者：Dokuburra Chanti Babu、Kankati Ashalatha、Chitturi Bhujanga Rao、Jon Paul Selvam Jondoss、Yenamandra Venkateswarlu

  DOI：10.1002/hlca.201100086

  日期：2011.12

  AbstractAn efficient and short total synthesis of (−)‐cleistenolide (1) from D‐mannitol with an overall yield of 23.6% is described. The chiron approach for the synthesis of (−)‐cleistenolide involves a one‐C‐atom Wittig olefination, a selective allylic triethylsilyl protection, and a Grubbs‐catalyzed ring‐closure‐metathesis (RCM) reaction as the key steps.