(1S,2R)-1-[(1R)-1,2-dihydroxyethyl]-2-hydroxybut-3-en-1-yl prop-2-enoate | 1357379-98-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (1S,2R)-1-[(1R)-1,2-dihydroxyethyl]-2-hydroxybut-3-en-1-yl prop-2-enoate
• 英文别名: 1,2-dideoxy-D-arabino-hex-1-enitol 4-(prop-2-enoate)；[(2R,3S,4R)-1,2,4-trihydroxyhex-5-en-3-yl] prop-2-enoate
• CAS: 1357379-98-6
• 化学式: C₉H₁₄O₅
• 分子量: 202.207
• InChiKey: HBFZTGLMNLWLLW-BHNWBGBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1S,2R)-1-[(1R)-1,2-dihydroxyethyl]-2-hydroxybut-3-en-1-yl prop-2-enoate 在 吡啶 、 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 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：

  1,2-dideoxy-5,6-(1-methylethylidene)-3-O-(triethylsilyl)-D-arabino-hex-1-enitol 4-(prop-2-enoate) 在 Dowex-50 (H⁺) 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以94%的产率得到(1S,2R)-1-[(1R)-1,2-dihydroxyethyl]-2-hydroxybut-3-en-1-yl 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.