ethyl (E)-7-[(1R,2R,5S,7R)-5-[15-[(2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-hydroxypropoxy]pentadecyl]-2-hydroxy-6,8-dioxabicyclo[3.2.1]octan-7-yl]hept-2-enoate | 472965-51-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: ethyl (E)-7-[(1R,2R,5S,7R)-5-[15-[(2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-hydroxypropoxy]pentadecyl]-2-hydroxy-6,8-dioxabicyclo[3.2.1]octan-7-yl]hept-2-enoate
• CAS: 472965-51-8
• 化学式: C₄₈H₇₁NO₉
• 分子量: 806.093
• InChiKey: UAPCZIGRZSMGMZ-QVMOQUCSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.8
• 重原子数：
  58
• 可旋转键数：
  31
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  133
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  ethyl (E)-7-[(1R,2R,5S,7R)-5-[15-[(2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-hydroxypropoxy]pentadecyl]-2-hydroxy-6,8-dioxabicyclo[3.2.1]octan-7-yl]hept-2-enoate 在 pyridine-SO3 complex 、 sodium sulfate 、 哌啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以27%的产率得到(+)-didemniserinolipid B
  参考文献：
  名称：

  Synthesis of (+)-Didemniserinolipid B via Ketalization/Ring-Closing Metathesis

  摘要：

  A modular synthesis of didemniserinolipid B is reported. Central to this synthesis was the use of a ketalization/ring-closing metathesis (K/RCM) strategy to establish the 6,8-dioxabicyclo[3.2.1]octane core. The C10 axial alcohol was established via a selective epoxidation, followed by reductive trans-diaxial epoxide opening. The serinol and unsaturated ester side chains were introduced by a Williamson etherification and cross metathesis, respectively.

  DOI：

  10.1021/ol702454m
• 作为产物：
  描述：

  (E)-ethyl-7-((1R,5S,7R)-5-(15-((R)-2-amino-3-hydroxy-propoxy)-pentadecyl)-2-hydroxy-6,8-dioxa-bicyclo[3.2.1]-octan-7-yl)hept-2-enoate hydrochloride 、 9-芴甲基-N-琥珀酰亚胺基碳酸酯 在 potassium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.5h， 以155.1 mg的产率得到ethyl (E)-7-[(1R,2R,5S,7R)-5-[15-[(2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-hydroxypropoxy]pentadecyl]-2-hydroxy-6,8-dioxabicyclo[3.2.1]octan-7-yl]hept-2-enoate
  参考文献：
  名称：

  Synthesis of (+)-Didemniserinolipid B via Ketalization/Ring-Closing Metathesis

  摘要：

  A modular synthesis of didemniserinolipid B is reported. Central to this synthesis was the use of a ketalization/ring-closing metathesis (K/RCM) strategy to establish the 6,8-dioxabicyclo[3.2.1]octane core. The C10 axial alcohol was established via a selective epoxidation, followed by reductive trans-diaxial epoxide opening. The serinol and unsaturated ester side chains were introduced by a Williamson etherification and cross metathesis, respectively.

  DOI：

  10.1021/ol702454m

文献信息

• Synthesis of (+)-Didemniserinolipid B via Ketalization/Ring-Closing Metathesis
  作者：Christopher C. Marvin、Eric A. Voight、Steven D. Burke

  DOI：10.1021/ol702454m

  日期：2007.12.1

  A modular synthesis of didemniserinolipid B is reported. Central to this synthesis was the use of a ketalization/ring-closing metathesis (K/RCM) strategy to establish the 6,8-dioxabicyclo[3.2.1]octane core. The C10 axial alcohol was established via a selective epoxidation, followed by reductive trans-diaxial epoxide opening. The serinol and unsaturated ester side chains were introduced by a Williamson etherification and cross metathesis, respectively.