(+/-)-1'-benzyl 3-tert-butyl 2-oxa-3-azaspiro[bicyclo[2.2.1]-hept[5]ene-7,4'-piperidine]-1',3-dicarboxylate | 1380494-44-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂螺癸烷衍生物
• 英文名称: (+/-)-1'-benzyl 3-tert-butyl 2-oxa-3-azaspiro[bicyclo[2.2.1]-hept[5]ene-7,4'-piperidine]-1',3-dicarboxylate
• 英文别名: 1-O'-benzyl 3-O-tert-butyl spiro[2-oxa-3-azabicyclo[2.2.1]hept-5-ene-7,4'-piperidine]-1',3-dicarboxylate
• CAS: 1380494-44-9
• 化学式: C₂₂H₂₈N₂O₅
• 分子量: 400.475
• InChiKey: WYNRDXXZHXMTJT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 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：

  (+/-)-1'-benzyl 3-tert-butyl 2-oxa-3-azaspiro[bicyclo[2.2.1]-hept[5]ene-7,4'-piperidine]-1',3-dicarboxylate 在 sodium tetrahydroborate 、 molybdenum hexacarbonyl 作用下， 以 水 、 乙腈 为溶剂， 反应 8.0h， 以90%的产率得到(+/-)-(1SR,4RS)-benzyl 1-(tert-butoxycarbonylamino)-4-hydroxy-8-azaspiro[4.5]dec-2-ene-8-carboxylate
  参考文献：
  名称：

  Diastereoselective Synthesis of a Spironoraristeromycin Using an Acylnitroso Diels−Alder Reaction^†† We dedicate this paper to Prof. Jeremiah P. Freeman on the occasion of his 80th birthday and with deep gratitude for his 25 years of service to organic chemistry as secretary ofOrganic Syntheses.

  摘要：

  The tert-butyl N-hydroxycarbamate-derived nitroso reagent I reacted with N-Cbz-protected spirocyclic diene 2 to provide spirocycloadduct 3. Here we describe the efficient conversion of 3 into the novel carbocyclic nucleoside spironoraristeromycin 4.

  DOI：

  10.1021/jo900877b
• 作为产物：
  描述：

  N-羟基氨基甲酸叔丁酯 、 benzyl 8-azaspiro[4.5]deca-1,3-diene-8-carboxylate 在 sodium periodate 作用下， 以 甲醇 、 水 为溶剂， 以61%的产率得到(+/-)-1'-benzyl 3-tert-butyl 2-oxa-3-azaspiro[bicyclo[2.2.1]-hept[5]ene-7,4'-piperidine]-1',3-dicarboxylate
  参考文献：
  名称：

  Diastereoselective Synthesis of a Spironoraristeromycin Using an Acylnitroso Diels−Alder Reaction^†† We dedicate this paper to Prof. Jeremiah P. Freeman on the occasion of his 80th birthday and with deep gratitude for his 25 years of service to organic chemistry as secretary ofOrganic Syntheses.

  摘要：

  The tert-butyl N-hydroxycarbamate-derived nitroso reagent I reacted with N-Cbz-protected spirocyclic diene 2 to provide spirocycloadduct 3. Here we describe the efficient conversion of 3 into the novel carbocyclic nucleoside spironoraristeromycin 4.

  DOI：

  10.1021/jo900877b