methyl (1R,3S,5R)-3-tert-(butyldiphenylsilyloxy)-5-tosyloxycyclohexanecarboxylate | 326599-39-7

• 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: methyl (1R,3S,5R)-3-tert-(butyldiphenylsilyloxy)-5-tosyloxycyclohexanecarboxylate
• 英文别名: Methyl (1R,3S,5R)-3-t-butyldiphenylsilyloxy-5-tosyloxy-cyclohexane-carboxylate；methyl (1R,3S,5R)-3-[tert-butyl(diphenyl)silyl]oxy-5-(4-methylphenyl)sulfonyloxycyclohexane-1-carboxylate
• CAS: 326599-39-7
• 化学式: C₃₁H₃₈O₆SSi
• 分子量: 566.791
• InChiKey: FENXFVOOMDLVOP-NXCFDTQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.99
• 重原子数：
  39
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  87.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (1R,3S,5R)-3-tert-(butyldiphenylsilyloxy)-5-tosyloxycyclohexanecarboxylate 在 potassium tert-butylate 、 二异丁基氢化铝 作用下， 以 甲苯 、 叔丁醇 为溶剂， 反应 2.5h， 生成 [(1S,3R,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-bicyclo[3.1.0]hex-1-yl]-methanol
  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 carbonate 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.5h， 生成 methyl (1R,3S,5R)-3-tert-(butyldiphenylsilyloxy)-5-tosyloxycyclohexanecarboxylate
  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