[(1R,2S)-1-benzoyloxy-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-oxopropan-2-yl] benzoate | 897954-00-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [(1R,2S)-1-benzoyloxy-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-oxopropan-2-yl] benzoate
• CAS: 897954-00-6
• 化学式: C₂₂H₂₂O₇
• 分子量: 398.412
• InChiKey: UGMBUENAHITCDH-QRVBRYPASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [(1R,2S)-1-benzoyloxy-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-oxopropan-2-yl] benzoate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以2.4 g的产率得到(1'R,2R,3S)-1-(2',2'-dimethyl-[1',3']dioxolan-4'-yl)-propane-1,2,3-triol
  参考文献：
  名称：

  Studies directed toward the first total synthesis of acremodiol and acremonol

  摘要：

  Studies directed toward the synthesis of acremodiol and acremonol resulted in the synthesis of two macrodiolides 1, la, and 2 besides 3. The attempted synthesis of 1 and 2 confirmed that the absolute stereochemistry defined in the earlier report is incorrect. Compound I was synthesized by RCM-mediated macrocyclization. Attempted synthesis of 2 failed to give good yields in the cyclization, and la and 2 were synthesized by the Yamaguchi macrolactonization method. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.10.030
• 作为产物：
  描述：

  甘露醇 在 对甲苯磺酸 、 高碘酸 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 18.5h， 生成 [(1R,2S)-1-benzoyloxy-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-oxopropan-2-yl] benzoate
  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.
• Studies directed toward the first total synthesis of acremodiol and acremonol
  作者：Gangavaram V.M. Sharma、Samala Mallesham、Chirutha Chandra Mouli

  DOI：10.1016/j.tetasy.2009.10.030

  日期：2009.11

  Studies directed toward the synthesis of acremodiol and acremonol resulted in the synthesis of two macrodiolides 1, la, and 2 besides 3. The attempted synthesis of 1 and 2 confirmed that the absolute stereochemistry defined in the earlier report is incorrect. Compound I was synthesized by RCM-mediated macrocyclization. Attempted synthesis of 2 failed to give good yields in the cyclization, and la and 2 were synthesized by the Yamaguchi macrolactonization method. (C) 2009 Elsevier Ltd. All rights reserved.