tert-butyl((3aS,4S,6S,6aS)-6-(4-methoxybenzyloxy)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yloxy)-dimethylsilane | 1159952-81-4

• 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((3aS,4S,6S,6aS)-6-(4-methoxybenzyloxy)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yloxy)-dimethylsilane
• CAS: 1159952-81-4
• 化学式: C₂₂H₃₆O₅Si
• 分子量: 408.61
• InChiKey: XCILJMMRQDADEE-LWYYNNOASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.89
• 重原子数：
  28.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  46.15
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  tert-butyl((3aS,4S,6S,6aS)-6-(4-methoxybenzyloxy)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yloxy)-dimethylsilane 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以89%的产率得到(3aR,4S,6S,6aS)-6-(4-methoxybenzyloxy)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ol
  参考文献：
  名称：

  A new synthesis and an antiviral assessment of the 4′-fluoro derivative of 4′-deoxy-5′-noraristeromycin

  摘要：

  A synthetic route to (1S, 2S, 3R, 5S)-3-(6-amino-9H-purin-9-yl)-5-fluorocyclopentane-1,2-diol (that is, the 4'-fluoro derivative of 4'-deoxy-5'-noraristeromycin, 3) is described via a fluorinated cyclopentanol, which is in contrast to existing schemes where fluorination occurred once the purine ring was present. Compound 3 was assayed versus a number of viruses. A favorable response was observed towards measles (IC50 of 1.2 mu g/mL in the neutral red assay and 14 mu g/mL by the visual assay) but this was accompanied by cytotoxicity in the CV-1 host cells (21-36 mu g/mL). Among the viruses unaffected by 3 were human cytomegalovirus and the poxviruses (vaccinia and cowpox), which are three viruses that were inhibited by the 40,40-difluoro analog of 3 (that is, 2). (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.03.004
• 作为产物：
  描述：

  (3aS,4S,6S,6aS)-2,2-dimethyl-6-(tert-butyldimethylsilyl)-tetrahydro-3aH-cyclopenta[d][1,3]-4-ol 、 4-甲氧基氯苄 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 以84%的产率得到tert-butyl((3aS,4S,6S,6aS)-6-(4-methoxybenzyloxy)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yloxy)-dimethylsilane
  参考文献：
  名称：

  A new synthesis and an antiviral assessment of the 4′-fluoro derivative of 4′-deoxy-5′-noraristeromycin

  摘要：

  A synthetic route to (1S, 2S, 3R, 5S)-3-(6-amino-9H-purin-9-yl)-5-fluorocyclopentane-1,2-diol (that is, the 4'-fluoro derivative of 4'-deoxy-5'-noraristeromycin, 3) is described via a fluorinated cyclopentanol, which is in contrast to existing schemes where fluorination occurred once the purine ring was present. Compound 3 was assayed versus a number of viruses. A favorable response was observed towards measles (IC50 of 1.2 mu g/mL in the neutral red assay and 14 mu g/mL by the visual assay) but this was accompanied by cytotoxicity in the CV-1 host cells (21-36 mu g/mL). Among the viruses unaffected by 3 were human cytomegalovirus and the poxviruses (vaccinia and cowpox), which are three viruses that were inhibited by the 40,40-difluoro analog of 3 (that is, 2). (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.03.004