3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-N1-pivaloyloxymethylinosine | 163071-16-7

• 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: 3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-N1-pivaloyloxymethylinosine
• 英文别名: 3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-N¹-pivaloyloxymethylinosine
• CAS: 163071-16-7
• 化学式: C₂₈H₄₈N₄O₈Si₂
• 分子量: 624.882
• InChiKey: ZPCYSNXIZFWURR-HUBRGWSESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.35
• 重原子数：
  42.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  136.16
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-N1-pivaloyloxymethylinosine 在 tris-(dibenzylideneacetone)dipalladium(0) 、 四丁基氟化铵 、 三乙胺 、 1,4-双(二苯基膦)丁烷 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 生成 5'-O-dimethoxytrityl-N¹-pivaloyloxymethyl-2'-O-allylinosine
  参考文献：
  名称：

  Simplified and Cost Effective Syntheses of Fully Protected Phosphoramidite Monomers Suitable for the Assembly of Oligo(2′-O-allylribonucleotides)

  摘要：

  Simplified, high yielding syntheses of suitably protected 2'-O-allylribonucleoside-3'-O-phosphoramidites starting from standard ribonucleosides have been elucidated. Specific 2'-O-allylation is readily achieved using amidine protection of the exocyclic amino groups of adenosine and cytidine and in the case of guanosine the allylation is carried out on an easily prepared intermediate bearing transient protection of the lactam function.

  DOI：

  10.1080/15257779408010672
• 作为产物：
  描述：

  在 potassium carbonate 、 对甲苯磺酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-N1-pivaloyloxymethylinosine
  参考文献：
  名称：

  Simplified and Cost Effective Syntheses of Fully Protected Phosphoramidite Monomers Suitable for the Assembly of Oligo(2′-O-allylribonucleotides)

  摘要：

  Simplified, high yielding syntheses of suitably protected 2'-O-allylribonucleoside-3'-O-phosphoramidites starting from standard ribonucleosides have been elucidated. Specific 2'-O-allylation is readily achieved using amidine protection of the exocyclic amino groups of adenosine and cytidine and in the case of guanosine the allylation is carried out on an easily prepared intermediate bearing transient protection of the lactam function.

  DOI：

  10.1080/15257779408010672

文献信息

• Synthesis of Benzodithiol-2-yl-Substituted Nucleoside Derivatives as Lead Compounds Having Anti-Bovine Viral Diarrhea Virus Activity
  作者：Kohji Seio、Takahide Sasaki、Koichirou Yanagida、Masanori Baba、Mitsuo Sekine

  DOI：10.1021/jm049677d

  日期：2004.10.1

  Nucleoside derivatives having a benzodithiol-2-yl (BDT) group were synthesized and examined for their anti-bovine viral diarrhea virus (BVDV) activities. Other substituents structurally similar to the BDT group such as 1,3-benzodioxol-2-yl, benzimidazol-2-yl and 1-oxo-benzodithiol-2-yl groups were not effective as the pharmacophore. The anti-BVDV assay revealed that 2'-O-BDT-guanosine and 2'-O-BDT-inosine

  合成具有苯并二硫醇-2-基（BDT）基团的核苷衍生物，并检查其抗牛病毒性腹泻病毒（BVDV）的活性。结构上与BDT基团相似的其他取代基，例如1，3-苯并二恶唑-2-基，苯并咪唑-2-基和1-氧-苯并二硫醇-2-基均不能用作药效基团。抗BVDV分析表明，在本研究合成的核苷衍生物中，2'-O-BDT-鸟苷和2'-O-BDT-肌苷具有最强的抗BVDV活性。由于BVDV已被公认是人类丙型肝炎病毒（HCV）的替代物，因此BDT修饰的核苷可能成为寻找核苷型抗HCV药物（如病毒唑）的一类新型先导化合物。