2'-deoxy-2-fluoro-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)adenosine | 259528-01-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 2'-deoxy-2-fluoro-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)adenosine
• 英文别名: 3',5'-O-(1,1,3,3-Tetraisopropyl-1,3-disiloxanediyl)-2'-deoxy-2-fluoroadenosine；9-[(6aR,8R,9aS)-2,2,4,4-tetra(propan-2-yl)-6a,8,9,9a-tetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl]-2-fluoropurin-6-amine
• CAS: 259528-01-3
• 化学式: C₂₂H₃₈FN₅O₄Si₂
• 分子量: 511.744
• InChiKey: YPRCCRBJURHWTG-RCCFBDPRSA-N

物化性质

• 沸点：
  570.3±60.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.79
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  107
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2'-deoxy-2-fluoro-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)adenosine 在 四乙基氟化铵水合物 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以98%的产率得到2-fluoro-2'-deoxyadenosine
  参考文献：
  名称：

  A Convenient Synthesis of 2′-Deoxy-2-fluoroadenosine; a Potential Prodrug for Suicide Gene Therapy

  摘要：

  A convenient synthesis of 2'-deoxy-2-fluoro-adenosine (1) is described. Deaminative fluorination of 2-aminoadenosine (2) followed by silylation of the 3', 5'-hydroxyl groups gave the corresponding 2-fluoroadenosine derivative 4 in good yield. Thiocarbonylation of 4 to thiocarbonylimidazolyl derivative 5a followed by treatment with an excess of tris(trimethylsilyl)silane (TTMSS) and tert-butyl peroxide in toluene at 80 degrees C was found to affect an efficient deoxygenation to the corresponding 2'-deoxy derivative 6. Desilylation of 6 by Et4NF in CH3CN afforded 1 in high yield.

  DOI：

  10.1080/15257770008035007
• 作为产物：
  描述：

  2-fluoro-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)adenosine 在 4-二甲氨基吡啶 、 二叔丁基过氧化物 、 三(三甲基硅基)硅烷 作用下， 以 1,4-二氧六环 、 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 2.25h， 生成 2'-deoxy-2-fluoro-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)adenosine
  参考文献：
  名称：

  A Convenient Synthesis of 2′-Deoxy-2-fluoroadenosine; a Potential Prodrug for Suicide Gene Therapy

  摘要：

  A convenient synthesis of 2'-deoxy-2-fluoro-adenosine (1) is described. Deaminative fluorination of 2-aminoadenosine (2) followed by silylation of the 3', 5'-hydroxyl groups gave the corresponding 2-fluoroadenosine derivative 4 in good yield. Thiocarbonylation of 4 to thiocarbonylimidazolyl derivative 5a followed by treatment with an excess of tris(trimethylsilyl)silane (TTMSS) and tert-butyl peroxide in toluene at 80 degrees C was found to affect an efficient deoxygenation to the corresponding 2'-deoxy derivative 6. Desilylation of 6 by Et4NF in CH3CN afforded 1 in high yield.

  DOI：

  10.1080/15257770008035007

文献信息

• A Convenient Synthesis of 2′-Deoxy-2-fluoroadenosine; a Potential Prodrug for Suicide Gene Therapy
  作者：Abdalla E. A. Hassan、Anita T. Shortnacy-fowler、John A. Montgomery、John A. Secrist

  DOI：10.1080/15257770008035007

  日期：2000.3

  A convenient synthesis of 2'-deoxy-2-fluoro-adenosine (1) is described. Deaminative fluorination of 2-aminoadenosine (2) followed by silylation of the 3', 5'-hydroxyl groups gave the corresponding 2-fluoroadenosine derivative 4 in good yield. Thiocarbonylation of 4 to thiocarbonylimidazolyl derivative 5a followed by treatment with an excess of tris(trimethylsilyl)silane (TTMSS) and tert-butyl peroxide in toluene at 80 degrees C was found to affect an efficient deoxygenation to the corresponding 2'-deoxy derivative 6. Desilylation of 6 by Et4NF in CH3CN afforded 1 in high yield.