[(1R,2S)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-1-[(2S,3R)-2,3-dimethyl-4-phenylmethoxybutyl]-4-formyl-3-methylcyclohex-3-en-1-yl]methyl 2,2-dimethylpropanoate | 1119753-79-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: [(1R,2S)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-1-[(2S,3R)-2,3-dimethyl-4-phenylmethoxybutyl]-4-formyl-3-methylcyclohex-3-en-1-yl]methyl 2,2-dimethylpropanoate
• CAS: 1119753-79-5
• 化学式: C₄₄H₆₀O₅Si
• 分子量: 697.043
• InChiKey: VEIXBRBUSZCSHF-MNNYKGRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.94
• 重原子数：
  50
• 可旋转键数：
  18
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  [(1R,2S)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-1-[(2S,3R)-2,3-dimethyl-4-phenylmethoxybutyl]-4-formyl-3-methylcyclohex-3-en-1-yl]methyl 2,2-dimethylpropanoate 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 1.5h， 生成
  参考文献：
  名称：

  Studies Toward the Synthesis of Spirolides: Assembly of the Elaborated E-Ring Fragment

  摘要：

  A stereoselective synthesis of the spiroimine fragment of spirolide C is described. The congested C7 and C29 tertiary and quaternary centers are constructed by a diastereoselective Ireland-Claisen rearrangement. The E ring is completed by means of an aldol cyclocondensation. Additional studies were preformed on the advanced intermediate to probe a future coupling strategy.

  DOI：

  10.1021/ol8027797
• 作为产物：
  描述：

  [(2R,4S,5R)-2-[(2S)-1-[tert-butyl(diphenyl)silyl]oxy-3-oxobutan-2-yl]-4,5-dimethyl-2-(4-oxobutyl)-6-phenylmethoxyhexyl] 2,2-dimethylpropanoate 在 piperidinium trifluoroacetate 作用下， 以 甲苯 为溶剂， 反应 72.0h， 以91%的产率得到[(1R,2S)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-1-[(2S,3R)-2,3-dimethyl-4-phenylmethoxybutyl]-4-formyl-3-methylcyclohex-3-en-1-yl]methyl 2,2-dimethylpropanoate
  参考文献：
  名称：

  Studies Toward the Synthesis of Spirolides: Assembly of the Elaborated E-Ring Fragment

  摘要：

  A stereoselective synthesis of the spiroimine fragment of spirolide C is described. The congested C7 and C29 tertiary and quaternary centers are constructed by a diastereoselective Ireland-Claisen rearrangement. The E ring is completed by means of an aldol cyclocondensation. Additional studies were preformed on the advanced intermediate to probe a future coupling strategy.

  DOI：

  10.1021/ol8027797