(±)acetic acid 4-(t-butyldimethylsilanyloxymethyl)-4-vinyl-dihydro-furan-2-yl ester | 1404301-96-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: (±)acetic acid 4-(t-butyldimethylsilanyloxymethyl)-4-vinyl-dihydro-furan-2-yl ester
• CAS: 1404301-96-7
• 化学式: C₁₅H₂₈O₄Si
• 分子量: 300.47
• InChiKey: WYRAFLXBDUHNAC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.49
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  (±)acetic acid 4-(t-butyldimethylsilanyloxymethyl)-4-vinyl-dihydro-furan-2-yl ester 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 甲醇 、 硫酸氢铵 、 三甲基溴硅烷 、 palladium 10% on activated carbon 、 四丁基氟化铵 、 氨 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙腈 、 环己烯 为溶剂， 反应 117.0h， 生成 2-[(3S,5R)-5-(2-amino-6-oxo-1H-purin-9-yl)-3-(hydroxymethyl)oxolan-3-yl]ethylphosphonic acid
  参考文献：
  名称：

  Synthesis of Novel 3′-Hydroxymethyl 5′-Deoxythreosyl Phosphonic Acid Nucleoside Analogues as Potent Antiviral Agents

  摘要：

  A very efficient synthetic route to novel 3'-hydroxymethyl 5'-deoxythreosyl phosphonic acid nucleosides was described. The discovery of threosyl phosphonate nucleoside (PMDTA, EC50 = 2.53 mu M) as a potent antihuman immunodeficiency virus (anti-HIV) agent has led to the synthesis and biological evaluation of 3'-modified 5'-deoxy versions of the threosyl phosphonate nucleosides. 3'-Hydroxymethyl 5'-deoxythreosyl phosphonic acid nucleoside analogues 15, 19, 24, and 28 were synthesized from 1,3-dihydroxyacetone and tested for anti-HIV activity as well as cytotoxicity. The adenine analogue 19 exhibits moderate in vitro anti-HIV-1 activity (EC50 = 10.2 mu M).

  DOI：

  10.1080/15257770.2012.724134
• 作为产物：
  描述：

  (±)-4-(t-butyldimethylsilanyloxymethyl)-4-vinyl-dihydro-furan-2-one 在 吡啶 、 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 反应 0.25h， 生成 (±)acetic acid 4-(t-butyldimethylsilanyloxymethyl)-4-vinyl-dihydro-furan-2-yl ester
  参考文献：
  名称：

  Synthesis of Novel 3′-Hydroxymethyl 5′-Deoxythreosyl Phosphonic Acid Nucleoside Analogues as Potent Antiviral Agents

  摘要：

  A very efficient synthetic route to novel 3'-hydroxymethyl 5'-deoxythreosyl phosphonic acid nucleosides was described. The discovery of threosyl phosphonate nucleoside (PMDTA, EC50 = 2.53 mu M) as a potent antihuman immunodeficiency virus (anti-HIV) agent has led to the synthesis and biological evaluation of 3'-modified 5'-deoxy versions of the threosyl phosphonate nucleosides. 3'-Hydroxymethyl 5'-deoxythreosyl phosphonic acid nucleoside analogues 15, 19, 24, and 28 were synthesized from 1,3-dihydroxyacetone and tested for anti-HIV activity as well as cytotoxicity. The adenine analogue 19 exhibits moderate in vitro anti-HIV-1 activity (EC50 = 10.2 mu M).

  DOI：

  10.1080/15257770.2012.724134