tert-butyl ((1R,4R)-4-((tert-butyldiphenylsilyl)oxy)cyclopent-2-en-1-yl)((2-nitrophenyl)sulfonyl)carbamate | 817210-69-8

• 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: tert-butyl ((1R,4R)-4-((tert-butyldiphenylsilyl)oxy)cyclopent-2-en-1-yl)((2-nitrophenyl)sulfonyl)carbamate
• CAS: 817210-69-8
• 化学式: C₃₂H₃₈N₂O₇SSi
• 分子量: 622.814
• InChiKey: LEMWBHJUUILFQM-DQEYMECFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.79
• 重原子数：
  43.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  116.05
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  tert-butyl ((1R,4R)-4-((tert-butyldiphenylsilyl)oxy)cyclopent-2-en-1-yl)((2-nitrophenyl)sulfonyl)carbamate 在 lithium hydroxide 、 巯基乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以89%的产率得到tert-butyl N-[(1R,4R)-4-[tert-butyl(diphenyl)silyl]oxycyclopent-2-en-1-yl]carbamate
  参考文献：
  名称：

  Chiral base route to functionalised cyclopentenyl amines: formal synthesis of the cyclopentene core of nucleoside Q

  摘要：

  A chiral base route to a range of highly functionalised amino cyclopentenes has been developed. The key asymmetric step involved the chiral lithium amide base-mediated rearrangement of a protected trans-4-hydroxy cyclopentene oxide to give an allylic alcohol (88% ee). Subsequent Overman rearrangement gave a protected trans-1,2-aminocyclopentenol whereas Mitsunobu substitution with BocNHNs gave a protected cis-amino cyclopentenol. Both are proven intermediates for natural product synthesis. The protected cis-aminocyclopentenol was transformed in a few steps into a precursor of the cyclopentene core of nucleoside Q, a natural product whose deficiency in animals is related to tumour growth. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.10.043
• 作为产物：
  描述：

  tert-butyl(cyclopent-3-en-1-yloxy)diphenylsilane 在 偶氮二甲酸二异丙酯 、 间氯过氧苯甲酸 、 三苯基膦 、 (1R,2S)-N-methyl-1-phenyl-2-pyrrolidinopropanamine lithium amide 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 114.0h， 生成 tert-butyl ((1R,4R)-4-((tert-butyldiphenylsilyl)oxy)cyclopent-2-en-1-yl)((2-nitrophenyl)sulfonyl)carbamate
  参考文献：
  名称：

  Chiral base route to functionalised cyclopentenyl amines: formal synthesis of the cyclopentene core of nucleoside Q

  摘要：

  A chiral base route to a range of highly functionalised amino cyclopentenes has been developed. The key asymmetric step involved the chiral lithium amide base-mediated rearrangement of a protected trans-4-hydroxy cyclopentene oxide to give an allylic alcohol (88% ee). Subsequent Overman rearrangement gave a protected trans-1,2-aminocyclopentenol whereas Mitsunobu substitution with BocNHNs gave a protected cis-amino cyclopentenol. Both are proven intermediates for natural product synthesis. The protected cis-aminocyclopentenol was transformed in a few steps into a precursor of the cyclopentene core of nucleoside Q, a natural product whose deficiency in animals is related to tumour growth. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.10.043