3'-O-<(tert-butyl)dimethylsilyl>-5'-O-(monomethoxytrityl)-N⁶-<2-(4-nitrophenyl)ethoxycarbonyl>adenosine 2'-<2-(4-nitrophenyl)ethyl N,N-diisopropylphosphoramidite> | 156046-18-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 3'-O-<(tert-butyl)dimethylsilyl>-5'-O-(monomethoxytrityl)-N⁶-<2-(4-nitrophenyl)ethoxycarbonyl>adenosine 2'-<2-(4-nitrophenyl)ethyl N,N-diisopropylphosphoramidite>
• 英文别名: 3'-O-<(tert-butyl)dimethylsilyl>-5'-O-(monomethoxytrityl)-N⁶-<2-(4-nitrophenyl)ethoxycarbonyl>adenosine 2'-<2-(4-nitrophenyl)ethyl diisopropylphosphoramidite>；3'-O-[(tert-butyl)dimethylsilyl]-5'-O-(monomethoxytrityl)-N⁶-[2-(4-nitrophenyl)ethoxycarbonyl]adenosine 2'-[2-(4-nitrophenyl)ethyl N,N-diisopropylphosphoramidite]；2-(4-nitrophenyl)ethyl N-[9-[(2R,3R,4R,5R)-4-[tert-butyl(dimethyl)silyl]oxy-3-[[di(propan-2-yl)amino]-[2-(4-nitrophenyl)ethoxy]phosphanyl]oxy-5-[[(4-methoxyphenyl)-diphenylmethoxy]methyl]oxolan-2-yl]purin-6-yl]carbamate
• CAS: 156046-18-3
• 化学式: C₅₉H₇₁N₈O₁₂PSi
• 分子量: 1143.32
• InChiKey: RJJBRMHSCVJFQB-PIKOIADHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.73
• 重原子数：
  81
• 可旋转键数：
  25
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  232
• 氢给体数：
  1
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  3'-O-<(tert-butyl)dimethylsilyl>-5'-O-(monomethoxytrityl)-N⁶-<2-(4-nitrophenyl)ethoxycarbonyl>adenosine 2'-<2-(4-nitrophenyl)ethyl N,N-diisopropylphosphoramidite> 、 2'-O-<(tert-butyl)dimethylsilyl>-3'-deoxy-3'-(hexadecanoylamino)-N⁶-<2-(4-nitrophenyl)ethoxycarbonyl>adenosine 在 吡啶 、 四氮唑 、 水 、 碘 作用下， 生成 3'-O-<(tert-butyl)dimethylsilyl>-5'-O-(monomethoxytrityl)-N⁶-<2-(4-nitrophenyl)ethoxycarbonyl>adenylyl-<2'-P-<2-(4-nitrophenyl)ethyl>>-5'>-2'-O-<(tert-butyl)dimethylsilyl>-3'-deoxy-3'-(hexadecanoylamino)-N⁶-<2-(4-nitrophenyl)ethoxycarbonyl>ad...
  参考文献：
  名称：

  Nucleotides, Part LIX, Synthesis, Characterization, and Biological Activities of New Potential Antiviral Agents: (2′ - 5′)Adenylate Trimer Analogs Containing 3′-Deoxy-3′-(hexadecanoylamino)adenosine at the 2′-Terminus

  摘要：

  Based upon 3'-amino-3'-deoxyadenosine (15), its protected 3'-hexadecanoylamino derivative 22 was chosen as starting material for the synthesis of a series of new modified 2'-5'-adenylate trimers 33-36 as potential antiviral agents. All (2'-5')A trimer analogs 33-36 inhibit HIV-1 replication as measured by the inhibition of syncytia formation and inhibition of HIV-1 reverse transcriptase activity. Compound 34 inhibits HIV-1 reverse transcription by 100% and subsequently inhibits expression of HIV-1 p24. However, compound 35 acts differently, since it does not inhibit HIV-1 reverse transcription, HIV-1 integrase, or HIV-1 p24 expression. Therefore, 35 appears to exert its inhibitory effect at a later stage of HIV-1 replication, i.e., the budding process.

  DOI：

  10.1002/(sici)1522-2675(19990407)82:4<597::aid-hlca597>3.0.co;2-v
• 作为产物：
  描述：

  1-氯-2-(4-硝基苯基)乙烷 在 四氮唑 作用下， 以 乙醚 、 乙腈 为溶剂， 反应 32.25h， 生成 3'-O-<(tert-butyl)dimethylsilyl>-5'-O-(monomethoxytrityl)-N⁶-<2-(4-nitrophenyl)ethoxycarbonyl>adenosine 2'-<2-(4-nitrophenyl)ethyl N,N-diisopropylphosphoramidite>
  参考文献：
  名称：

  核苷酸部分XL。修饰的2'–5'腺苷酸三聚体-潜在的抗病毒药的合成和表征†

  摘要：

  通过亚磷酰胺法合成了在各种糖部分的3'-OH位置带有（叔丁基）二甲基甲硅烷基（tbds）的2'-5'腺苷酸三聚体41-44。比较了（叔丁氧基）羰基（boc）和2-（4-硝基苯基）乙基磺酰基（npes）基团在3'- O- tbds残基附近用于2'-OH保护的用途。目标三聚体。对于其他功能位置，赞成使用2-（4-硝基苯基）乙基（npe）和2-（4-硝基苯基）乙氧基羰基（npeoc）保护基。

  DOI：

  10.1002/hlca.19940770104

文献信息

• Nucleotides
  作者：Evgeny I. Kvasyuk、Igor A. Mikhailopulo、Joseph W. Homan、Kathryn T. Iacono、Nicholas F. Muto、Robert J. Suhadolnik、Wolfgang Pfleiderer

  DOI：10.1002/(sici)1522-2675(19990113)82:1<19::aid-hlca19>3.0.co;2-g

  日期：1999.1.13