methyl(2R,3aS,4aS)-2-(tert-butyldiphenylsilyloxy)bicyclo[3.1.0]-hexane-3a-carboxylate | 326599-40-0

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: methyl(2R,3aS,4aS)-2-(tert-butyldiphenylsilyloxy)bicyclo[3.1.0]-hexane-3a-carboxylate
• 英文别名: methyl (1S,3R,5S)-3-[tert-butyl(diphenyl)silyl]oxybicyclo[3.1.0]hexane-1-carboxylate
• CAS: 326599-40-0
• 化学式: C₂₄H₃₀O₃Si
• 分子量: 394.586
• InChiKey: DVIUOZMTHAUNEV-IECBHUPTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl(2R,3aS,4aS)-2-(tert-butyldiphenylsilyloxy)bicyclo[3.1.0]-hexane-3a-carboxylate 在 叔丁基锂 、 二异丁基氢化铝 、 对甲苯磺酸 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 水 、 甲苯 、 正戊烷 为溶剂， 反应 7.5h， 生成 (1R,3E,5S)-3-[(2E)-2-[(1R,3aR,7aR)-1-[(2R)-6-hydroxy-6-methylhept-4-yn-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-5-[tert-butyl(diphenyl)silyl]oxycyclohexan-1-ol
  参考文献：
  名称：

  A Practical Synthesis of 14-epi-19-nor-1α,25-Dihydroxyvitamin D3 Analogues and Their A-ring Epimers

  摘要：

  A practical synthesis of (2S,3aS,4aS)-2-tert-butyldimethylsilyloxybicyclo[3.1.0]hexane-3a-carbaldehyde (14a) and diastereoisomers, starting from all-cis methyl 3,5-dihydroxy-1-cyclohexanecarboxylate (24) is described. Coupling with appropriate cis-hydrindanes produces the title compounds. TX 522, a member of this series, is currently in phase II clinical studies for the treatment of psoriasis. The key step involves the coupling of 14 and 16 with the respective cis-hydrindanes 9 and 7.

  DOI：

  10.1002/1099-0690(200110)2001:20<3779::aid-ejoc3779>3.0.co;2-q
• 作为产物：
  描述：

  (1S,3S,5R)-3-acetoxy-5-hydroxy-1-(methoxycarbonyl)cyclohexane 在 咪唑 、 4-二甲氨基吡啶 、 potassium tert-butylate 、 potassium carbonate 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 23.5h， 生成 methyl(2R,3aS,4aS)-2-(tert-butyldiphenylsilyloxy)bicyclo[3.1.0]-hexane-3a-carboxylate
  参考文献：
  名称：

  A Practical Synthesis of 14-epi-19-nor-1α,25-Dihydroxyvitamin D3 Analogues and Their A-ring Epimers

  摘要：

  A practical synthesis of (2S,3aS,4aS)-2-tert-butyldimethylsilyloxybicyclo[3.1.0]hexane-3a-carbaldehyde (14a) and diastereoisomers, starting from all-cis methyl 3,5-dihydroxy-1-cyclohexanecarboxylate (24) is described. Coupling with appropriate cis-hydrindanes produces the title compounds. TX 522, a member of this series, is currently in phase II clinical studies for the treatment of psoriasis. The key step involves the coupling of 14 and 16 with the respective cis-hydrindanes 9 and 7.

  DOI：

  10.1002/1099-0690(200110)2001:20<3779::aid-ejoc3779>3.0.co;2-q

文献信息

• A Practical Synthesis of 14-epi-19-nor-1α,25-Dihydroxyvitamin D3 Analogues and Their A-ring Epimers
  作者：Yusheng Wu、Yurui Zhao、Honjian Tian、Pierre De Clercq、Maurits Vandewalle、Marielle Berthier、Gills Pellegrino、Philippe Maillos、Jean-Claude Pascal

  DOI：10.1002/1099-0690(200110)2001:20<3779::aid-ejoc3779>3.0.co;2-q

  日期：2001.10

  A practical synthesis of (2S,3aS,4aS)-2-tert-butyldimethylsilyloxybicyclo[3.1.0]hexane-3a-carbaldehyde (14a) and diastereoisomers, starting from all-cis methyl 3,5-dihydroxy-1-cyclohexanecarboxylate (24) is described. Coupling with appropriate cis-hydrindanes produces the title compounds. TX 522, a member of this series, is currently in phase II clinical studies for the treatment of psoriasis. The key step involves the coupling of 14 and 16 with the respective cis-hydrindanes 9 and 7.