tert-butyl (1R,2S)-1-allyl-2-((S)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)cyclopentylcarbamate | 1148178-19-1

• 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: tert-butyl (1R,2S)-1-allyl-2-((S)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)cyclopentylcarbamate
• 英文别名: tert-butyl N-[(1R,2S)-2-[(2S)-1-[tert-butyl(diphenyl)silyl]oxypropan-2-yl]-1-prop-2-enylcyclopentyl]carbamate
• CAS: 1148178-19-1
• 化学式: C₃₂H₄₇NO₃Si
• 分子量: 521.816
• InChiKey: SKEGCCURJOZUIC-XSFHMJGTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.84
• 重原子数：
  37
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl (1R,2S)-1-allyl-2-((S)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)cyclopentylcarbamate 、 3-iodoacrylic acid methyl ester 在 9-硼双环[3.3.1]壬烷 、 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 三苯胂 、 caesium carbonate 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 以76%的产率得到methyl (E)-6-((1R,2S)-1-(tert-butoxycarbonylamino)-2-((S)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)cyclopentyl)hex-2-enoate
  参考文献：
  名称：

  Asymmetric Construction of Three Contiguous Stereogenic Centers by Conjugate Addition−Alkylation of Lithium Ester Enolate

  摘要：

  A chiral ligand- and lithium amide-assisted asymmetric conjugate addition of lithium enolate of propionate to cyclopentenecarboxylate gave the corresponding lithium enolate, whose allylation gave the key intermediate of the marine alkaloid halichlorine as a single diastereomer with moderate enantioselectivity.

  DOI：

  10.1021/ol900447n
• 作为产物：
  描述：

  tert-butyl (1R,2S)-1-allyl-2-((S)-1-hydroxypropan-2-yl)cyclopentylcarbamate 、 叔丁基二苯基氯硅烷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以96%的产率得到tert-butyl (1R,2S)-1-allyl-2-((S)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)cyclopentylcarbamate
  参考文献：
  名称：

  Asymmetric Construction of Three Contiguous Stereogenic Centers by Conjugate Addition−Alkylation of Lithium Ester Enolate

  摘要：

  A chiral ligand- and lithium amide-assisted asymmetric conjugate addition of lithium enolate of propionate to cyclopentenecarboxylate gave the corresponding lithium enolate, whose allylation gave the key intermediate of the marine alkaloid halichlorine as a single diastereomer with moderate enantioselectivity.

  DOI：

  10.1021/ol900447n

文献信息

• Asymmetric Construction of Three Contiguous Stereogenic Centers by Conjugate Addition−Alkylation of Lithium Ester Enolate
  作者：Yasutomo Yamamoto、Yorinobu Yasuda、Hiroyuki Nasu、Kiyoshi Tomioka

  DOI：10.1021/ol900447n

  日期：2009.5.7

  A chiral ligand- and lithium amide-assisted asymmetric conjugate addition of lithium enolate of propionate to cyclopentenecarboxylate gave the corresponding lithium enolate, whose allylation gave the key intermediate of the marine alkaloid halichlorine as a single diastereomer with moderate enantioselectivity.