(3R,1'S,2'S)-5-tert-Butyldiphenylsiloxy-3-methyl-3-(1'-phenyl-2'-trifluoroacetamido-1'-propoxy)-1-pentanal | 247256-57-1

• 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: (3R,1'S,2'S)-5-tert-Butyldiphenylsiloxy-3-methyl-3-(1'-phenyl-2'-trifluoroacetamido-1'-propoxy)-1-pentanal
• 英文别名: N-[(1S,2S)-1-[(3R)-1-[tert-butyl(diphenyl)silyl]oxy-3-methyl-5-oxopentan-3-yl]oxy-1-phenylpropan-2-yl]-2,2,2-trifluoroacetamide
• CAS: 247256-57-1
• 化学式: C₃₃H₄₀F₃NO₄Si
• 分子量: 599.766
• InChiKey: JRDITALWZTUXPR-BVKYAAJPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.13
• 重原子数：
  42
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (3R,1'S,2'S)-5-tert-Butyldiphenylsiloxy-3-methyl-3-(1'-phenyl-2'-trifluoroacetamido-1'-propoxy)-1-pentanal 在 氨 、 sodium 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 5.5h， 生成 (3R,5RS)-1-tert-Butyldiphenylsiloxy-3,7-dimethyl-3,5-octanediol p-methoxybenzylidenacetal
  参考文献：
  名称：

  First Total Synthesis and Determination of the Absolute Configuration of the Stress Factor (+)-Hydroxymyoporone

  摘要：

  The first total synthesis of the stress factor (+)-hydroxymyoporone (4) is presented. The key step is an asymmetric allylation of the methyl ketone 10 which proceeds with excellent selectivity and yield. In addition, it was proven that the allylation assignment of the absolute configuration of hydroxymyoporone published in the natural literature is incorrect; the correct structure of the (+)-enantiomer is depicted in the structural formula 4.

  DOI：

  10.1002/(sici)1521-3765(19991001)5:10<2885::aid-chem2885>3.0.co;2-8
• 作为产物：
  描述：

  4-((tert-butyldiphenylsilyl)oxy)butan-2-one 在 三氟甲磺酸 、 臭氧 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 5.5h， 生成 (3R,1'S,2'S)-5-tert-Butyldiphenylsiloxy-3-methyl-3-(1'-phenyl-2'-trifluoroacetamido-1'-propoxy)-1-pentanal
  参考文献：
  名称：

  First Total Synthesis and Determination of the Absolute Configuration of the Stress Factor (+)-Hydroxymyoporone

  摘要：

  The first total synthesis of the stress factor (+)-hydroxymyoporone (4) is presented. The key step is an asymmetric allylation of the methyl ketone 10 which proceeds with excellent selectivity and yield. In addition, it was proven that the allylation assignment of the absolute configuration of hydroxymyoporone published in the natural literature is incorrect; the correct structure of the (+)-enantiomer is depicted in the structural formula 4.

  DOI：

  10.1002/(sici)1521-3765(19991001)5:10<2885::aid-chem2885>3.0.co;2-8