tert-butyl (4S)-4-[15-[(1R,2R,5S,7R)-7-[(E)-7-ethoxy-7-oxohept-5-enyl]-2-hydroxy-6,8-dioxabicyclo[3.2.1]octan-5-yl]pentadecoxymethyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate | 1004537-70-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: tert-butyl (4S)-4-[15-[(1R,2R,5S,7R)-7-[(E)-7-ethoxy-7-oxohept-5-enyl]-2-hydroxy-6,8-dioxabicyclo[3.2.1]octan-5-yl]pentadecoxymethyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 1004537-70-5
• 化学式: C₄₁H₇₃NO₉
• 分子量: 724.032
• InChiKey: VHYVHRZBKYWBDZ-JFTDYKDKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.9
• 重原子数：
  51
• 可旋转键数：
  28
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  tert-butyl (4S)-4-[15-[(1R,2R,5S,7R)-7-[(E)-7-ethoxy-7-oxohept-5-enyl]-2-hydroxy-6,8-dioxabicyclo[3.2.1]octan-5-yl]pentadecoxymethyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 48.0h， 以75%的产率得到(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
  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：

  在 三乙胺 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以89%的产率得到tert-butyl (4S)-4-[15-[(1R,2R,5S,7R)-7-[(E)-7-ethoxy-7-oxohept-5-enyl]-2-hydroxy-6,8-dioxabicyclo[3.2.1]octan-5-yl]pentadecoxymethyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
  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.