(1R,4R,5S,6R)-6-(((tert-butyldiphenylsilyl)oxy)methyl)-5-(dimethoxymethyl)bicyclo[2.2.1]heptan-2-one | 1226896-08-7

• 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: (1R,4R,5S,6R)-6-(((tert-butyldiphenylsilyl)oxy)methyl)-5-(dimethoxymethyl)bicyclo[2.2.1]heptan-2-one
• CAS: 1226896-08-7
• 化学式: C₂₇H₃₆O₄Si
• 分子量: 452.666
• InChiKey: SIVRIFDBDIQEKG-BRXVMWLGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.02
• 重原子数：
  32.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (1R,4R,5S,6R)-6-(((tert-butyldiphenylsilyl)oxy)methyl)-5-(dimethoxymethyl)bicyclo[2.2.1]heptan-2-one 在 potassium dihydrogenphosphate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以81%的产率得到(1R,5R,6S,7S)-7-(((tert-butyldiphenylsilyl)oxy)methyl)-6-(dimethoxymethyl)-2-oxabicyclo[3.2.1]octan-3-one
  参考文献：
  名称：

  Bioisostere of valtrate, anti-HIV principle by inhibition for nuclear export of Rev

  摘要：

  Rational design by the MO calculation disclosed 5,6-dihydrovaltrate (2) as the bioisostere of valtrate (1), the Rev-export inhibitor with anti-HIV activity. The synthesis of 2 was accomplished by ingenious use of asymmetric Diels-Alder reaction and stereoselective epoxidation associated with the adjacent hydroxyl group. Because of similar biological potency to 1, the analog 2 should be recognized as a promising scaffold for new anti-HIV agents with an unprecedented mechanism of action, inhibition for nuclear export of Rev protein, in the conventional remedy. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.02.038
• 作为产物：
  描述：

  甲氧基三甲基硅烷 、 (1R,2S,3R,4R)-3-(((tert-butyldiphenylsilyl)oxy)methyl)-5-oxobicyclo[2.2.1]heptane-2-carbaldehyde 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 以80%的产率得到(1R,4R,5S,6R)-6-(((tert-butyldiphenylsilyl)oxy)methyl)-5-(dimethoxymethyl)bicyclo[2.2.1]heptan-2-one
  参考文献：
  名称：

  Bioisostere of valtrate, anti-HIV principle by inhibition for nuclear export of Rev

  摘要：

  Rational design by the MO calculation disclosed 5,6-dihydrovaltrate (2) as the bioisostere of valtrate (1), the Rev-export inhibitor with anti-HIV activity. The synthesis of 2 was accomplished by ingenious use of asymmetric Diels-Alder reaction and stereoselective epoxidation associated with the adjacent hydroxyl group. Because of similar biological potency to 1, the analog 2 should be recognized as a promising scaffold for new anti-HIV agents with an unprecedented mechanism of action, inhibition for nuclear export of Rev protein, in the conventional remedy. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.02.038