(1S,4S,5R,7R)-4-((tert-butyldimethylsilyloxy)methyl)-8,8-dimethyl-2-oxo-3-oxabicyclo[5.1.0]octan-5-yl benzoate | 1265883-24-6

• 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: (1S,4S,5R,7R)-4-((tert-butyldimethylsilyloxy)methyl)-8,8-dimethyl-2-oxo-3-oxabicyclo[5.1.0]octan-5-yl benzoate
• 英文别名: [(1S,4S,5R,7R)-4-[[tert-butyl(dimethyl)silyl]oxymethyl]-8,8-dimethyl-2-oxo-3-oxabicyclo[5.1.0]octan-5-yl] benzoate
• CAS: 1265883-24-6
• 化学式: C₂₃H₃₄O₅Si
• 分子量: 418.605
• InChiKey: HZHWXOCOZNKLOZ-AKHDSKFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.82
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1S,4S,5R,7R)-4-((tert-butyldimethylsilyloxy)methyl)-8,8-dimethyl-2-oxo-3-oxabicyclo[5.1.0]octan-5-yl benzoate 、 4-溴苯甲酰氯 在 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 水 、 二氯甲烷 为溶剂， 生成 [(1S,4S,5R,7R)-5-benzoyloxy-8,8-dimethyl-2-oxo-3-oxabicyclo[5.1.0]octan-4-yl]methyl 4-bromobenzoate
  参考文献：
  名称：

  Total Synthesis of Lathyranoic Acid A

  摘要：

  The first total synthesis of lathyranoic acid A (1) was accomplished stereoselectively in a linear sequence of 20 steps and an overall yield of 1.4%. This modular synthesis featured a cyclic, stereocontrolled Cu-catalyzed intramolecular cyclopropanation to construct the cis-cyclopropane unit, a Grubbs metathesis to construct the gamma-substituted cyclopentenone moiety, and an anion-mediated conjugate addition.

  DOI：

  10.1021/jo102033h
• 作为产物：
  描述：

  [(2S,3R)-1-[tert-butyl(dimethyl)silyl]oxy-2-hydroxy-6-methylhept-5-en-3-yl] benzoate 在 bis(N-tert-butylsalicylaldiminato)copper(II) 、 N,N-二甲基苯胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 1.75h， 生成 (1S,4S,5R,7R)-4-((tert-butyldimethylsilyloxy)methyl)-8,8-dimethyl-2-oxo-3-oxabicyclo[5.1.0]octan-5-yl benzoate
  参考文献：
  名称：

  Total Synthesis of Lathyranoic Acid A

  摘要：

  The first total synthesis of lathyranoic acid A (1) was accomplished stereoselectively in a linear sequence of 20 steps and an overall yield of 1.4%. This modular synthesis featured a cyclic, stereocontrolled Cu-catalyzed intramolecular cyclopropanation to construct the cis-cyclopropane unit, a Grubbs metathesis to construct the gamma-substituted cyclopentenone moiety, and an anion-mediated conjugate addition.

  DOI：

  10.1021/jo102033h

文献信息

• Total Synthesis of Lathyranoic Acid A
  作者：Li-Fang Yu、Hai-Ning Hu、Fa-Jun Nan

  DOI：10.1021/jo102033h

  日期：2011.3.4

  The first total synthesis of lathyranoic acid A (1) was accomplished stereoselectively in a linear sequence of 20 steps and an overall yield of 1.4%. This modular synthesis featured a cyclic, stereocontrolled Cu-catalyzed intramolecular cyclopropanation to construct the cis-cyclopropane unit, a Grubbs metathesis to construct the gamma-substituted cyclopentenone moiety, and an anion-mediated conjugate addition.