(3aS,4S,6S,6aS)-6-fluoro-4-(4-methoxybenzyloxy)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxole | 1159952-89-2

• 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: (3aS,4S,6S,6aS)-6-fluoro-4-(4-methoxybenzyloxy)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxole
• CAS: 1159952-89-2
• 化学式: C₁₆H₂₁FO₄
• 分子量: 296.339
• InChiKey: IULZIWDZQFVJGV-XQLPTFJDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.84
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (3aS,4S,6S,6aS)-6-fluoro-4-(4-methoxybenzyloxy)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxole 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 1.0h， 以86%的产率得到(3aS,4S,6S,6aS)-6-fluoro-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：

  (3aR,4R,6S,6aS)-6-(4-methoxybenzyloxy)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ol 在 吡啶 、 二乙胺基三氟化硫 作用下， 以 二氯甲烷 为溶剂， 以70%的产率得到(3aS,4S,6S,6aS)-6-fluoro-4-(4-methoxybenzyloxy)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxole
  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