(-)-[1R,3S,2(1E)]-3-(tert-butyldimethylsilyloxy)-2-[1-(N,N-diisopropylcarbamoyloxy)methylidene]cyclopentyl N,N-diisopropylcarbamate | 444673-20-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (-)-[1R,3S,2(1E)]-3-(tert-butyldimethylsilyloxy)-2-[1-(N,N-diisopropylcarbamoyloxy)methylidene]cyclopentyl N,N-diisopropylcarbamate
• 英文别名: [(E)-[(2S,5R)-2-[tert-butyl(dimethyl)silyl]oxy-5-[di(propan-2-yl)carbamoyloxy]cyclopentylidene]methyl] N,N-di(propan-2-yl)carbamate
• CAS: 444673-20-5
• 化学式: C₂₆H₅₀N₂O₅Si
• 分子量: 498.779
• InChiKey: IBKSCXIUAJAWPW-SWXNLADBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.93
• 重原子数：
  34
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  68.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (-)-[1R,3S,2(1E)]-3-(tert-butyldimethylsilyloxy)-2-[1-(N,N-diisopropylcarbamoyloxy)methylidene]cyclopentyl N,N-diisopropylcarbamate 在 四丁基氟化铵 、 水 作用下， 以 乙醚 为溶剂， 反应 2.0h， 以100%的产率得到(-)-[1R,3S,2(1Z)]-2-[1-(N,N-diisopropylcarbamoyloxy)methylidene]-3-hydroxycyclopentyl N,N-diisopropylcarbamate
  参考文献：
  名称：

  Synthesis of an Ethynyl Carbamate and Application for Enantioselective Cyclocarbolithiation

  摘要：

  [GRAPHICS]The intramolecular trans-cyclocarbolithiation of the alpha-lithiated 4-substituted 5-hexynyl carbamate (1S,4RS)-14 employing lithiodestannylation is presented. The 5-exo-dig cyclization products cis-/trans-16a were formed exclusively. The highly enantioenriched organotin precursor (S)-11 was synthesized via an asymmetric deprotonation of the corresponding alkyl carbarnate 10 by the chiral complex sec-butyllithium/(-)sparteine and subsequent substitution with tributyltin chloride.

  DOI：

  10.1021/ol0260674
• 作为产物：
  描述：

  (+)-(1S,4RS)-4-(tert-butyldimethylsilyloxy)-6-(N,N-diisopropylcarbamoyloxy)-1-tributylstannyl-5-hexynyl N,N-diisopropylcarbamate 在 正丁基锂 、 甲醇 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 Diisopropyl-carbamic acid (1S,3S)-3-(tert-butyl-dimethyl-silanyloxy)-2-[1-diisopropylcarbamoyloxy-meth-(E)-ylidene]-cyclopentyl ester 、 (-)-[1R,3S,2(1E)]-3-(tert-butyldimethylsilyloxy)-2-[1-(N,N-diisopropylcarbamoyloxy)methylidene]cyclopentyl N,N-diisopropylcarbamate 、 Diisopropyl-carbamic acid (1S,3R)-3-(tert-butyl-dimethyl-silanyloxy)-2-[1-diisopropylcarbamoyloxy-meth-(E)-ylidene]-cyclopentyl ester 、 (-)-[1R,3R,2(1E)]-3-(tert-butyldimethylsilyloxy)-2-[1-(N,N-diisopropylcarbamoyloxy)-methylidene]cyclopentyl N,N-diisopropylcarbamate
  参考文献：
  名称：

  Synthesis of an Ethynyl Carbamate and Application for Enantioselective Cyclocarbolithiation

  摘要：

  [GRAPHICS]The intramolecular trans-cyclocarbolithiation of the alpha-lithiated 4-substituted 5-hexynyl carbamate (1S,4RS)-14 employing lithiodestannylation is presented. The 5-exo-dig cyclization products cis-/trans-16a were formed exclusively. The highly enantioenriched organotin precursor (S)-11 was synthesized via an asymmetric deprotonation of the corresponding alkyl carbarnate 10 by the chiral complex sec-butyllithium/(-)sparteine and subsequent substitution with tributyltin chloride.

  DOI：

  10.1021/ol0260674