(±)-4-(t-butyldimethylsilanyloxymethyl)-4-vinyl-dihydro-furan-2-one | 1404301-92-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (±)-4-(t-butyldimethylsilanyloxymethyl)-4-vinyl-dihydro-furan-2-one
• 英文别名: 4-[[Tert-butyl(dimethyl)silyl]oxymethyl]-4-ethenyloxolan-2-one
• CAS: 1404301-92-3
• 化学式: C₁₃H₂₄O₃Si
• 分子量: 256.417
• InChiKey: BXNJRTCPVHSWLK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.13
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  在 咪唑 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 (±)-4-(t-butyldimethylsilanyloxymethyl)-4-vinyl-dihydro-furan-2-one
  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

文献信息

• Synthesis of Novel 2′-Fluoro-3′-Hydroxymethyl-5′-Deoxythreosyl Phosphonic Acid Nucleoside Analogues As Antiviral Agents
  作者：Kyung Mi Kim、Joon Hee Hong

  DOI：10.1080/15257770.2013.874561

  日期：2014.2

  5′-deoxyphosphonate analogues were designed and synthesized to mimic naturally occurring purine monophosphate from 1,3-dihydroxyacetone as starting material. The discovery of threosyl phosphonate nucleoside (PMDTA, EC50 = 2.53 μM) as a potent anti-HIV agent has led to the synthesis and biological evaluation of 2′,3′-modified 5′-deoxyversions of the threosyl phosphonate nucleosides. The synthesized 2′-fluoro-3′-hydroxymethyl

  设计并合成了一系列嘌呤5'-脱氧膦酸酯类似物，以模仿以1,3-二羟基丙酮为原料的天然存在的嘌呤单磷酸酯。苏糖基膦酸酯核苷（PMDTA，EC 50 = 2.53μM ）作为有效的抗HIV药物的发现导致了苏糖基膦酸酯核苷的2'，3'-修饰的5'-脱氧转化的合成和生物学评估。合成2'-氟-3'-羟甲基-5'- deoxythreosyl膦酸核苷类似物14，18，23，和27的抗HIV活性以及细胞毒性进行了试验。腺嘌呤类似物18表现出较弱的体外抗HIV-1活性（EC 50 = 19.2μM）。