N⁶,N⁶-dibenzoyladenosine | 51008-81-2

• 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: N⁶,N⁶-dibenzoyladenosine
• 英文别名: Adenosine, N,N-dibenzoyl-；N-benzoyl-N-[9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-6-yl]benzamide
• CAS: 51008-81-2
• 化学式: C₂₄H₂₁N₅O₆
• 分子量: 475.461
• InChiKey: MMAFGVQKTQHTJK-VEBYGKHWSA-N

物化性质

• 熔点：
  174-175 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  788.8±70.0 °C(Predicted)
• 密度：
  1.56±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  35
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  151
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N⁶,N⁶-dibenzoyladenosine 在 吡啶 、 ammonium hydroxide 作用下， 反应 0.08h， 以95%的产率得到N6-苯甲酰基腺苷
  参考文献：
  名称：

  An Improved Transient Method for the Synthesis ofN-Benzoylated Nucleosides

  摘要：

  The Jones' transient method for the synthesis of N-benzoylated nucleosides is improved by reducing the amounts of chlorotrimethylsilane (TMSCI) and benzoyl chloride to nearly equivalent quantities. The easy work-up and high yields of products are the major advantages of this approach. Jones' method is further simplified by omitting the addition of ammonium hydroxide. The utility of this modification for the preparation of some useful protected nucleosides is also presented.

  DOI：

  10.1081/scc-120017200
• 作为产物：
  描述：

  O^2'_,O3'_,O5'-tris-trimethylsilanyl-adenosine 在 吡啶 、 水 作用下， 反应 10.0h， 生成 N⁶,N⁶-dibenzoyladenosine
  参考文献：
  名称：

  An Improved Transient Method for the Synthesis ofN-Benzoylated Nucleosides

  摘要：

  The Jones' transient method for the synthesis of N-benzoylated nucleosides is improved by reducing the amounts of chlorotrimethylsilane (TMSCI) and benzoyl chloride to nearly equivalent quantities. The easy work-up and high yields of products are the major advantages of this approach. Jones' method is further simplified by omitting the addition of ammonium hydroxide. The utility of this modification for the preparation of some useful protected nucleosides is also presented.

  DOI：

  10.1081/scc-120017200

文献信息

• A photochromic ATP analogue driving a motor protein with reversible light-controlled motility: controlling velocity and binding manner of a kinesin–microtubule system in an in vitro motility assay
  作者：Takashi Kamei、Tuyoshi Fukaminato、Nobuyuki Tamaoki

  DOI：10.1039/c2cc33552b

  日期：——

  We synthesized two photochromic ATP analogues (ATP-Azos) featuring azobenzene derivatives tethered at the 2′ position of the ribose ring. In the presence of the ATP-Azo tethering p-tert-butylazobenzene, we observed reversible photo-control of the motility, velocity and binding manner, of a kinesin–microtubule system in an in vitro motility assay.

  我们合成两种具有荧光特性的ATP类似物（ATP-偶氮），其中联苯胺衍生物以2′位置与核糖环连接。当存在与对叔丁基偶氮苯连接的ATP-偶氮时，我们在体外运动试验中观察到动力蛋白-微管系统运动、速度和结合方式的可逆光控。
• Synthesis of 2′-O,3′-O bicyclic adenosine analogues using ring closing metathesis
  作者：Patricia Busca、Mélanie Etheve-Quelquejeu、Jean-Marc Valéry

  DOI：10.1016/j.tetlet.2003.10.059

  日期：2003.12

  2′-O,3′-O bicyclic adenosine derivatives is presented as the first examples of a new family of 13-membered ring bicyclic nucleoside analogues. Cyclisation was achieved through ring closing metathesis (RCM) on a diene intermediate using Grubbs’ catalyst. The Z and E isomers were purified and characterised.

  2′- O，3′- O双环腺苷衍生物的合成被提出作为新的13元环双环核苷类似物家族的第一个实例。环化是通过使用Grubbs催化剂在二烯中间体上进行闭环复分解（RCM）来实现的。的ž和ë异构体进行纯化和表征。
• Preparation of Zwitterionic Ribonucleoside Phosphoramidites for Solid-Phase siRNA Synthesis
  作者：Romualdas Smicius、Joachim W. Engels

  DOI：10.1021/jo800451m

  日期：2008.7.1

  RNA oligomers, carrying 2'-O-modified nucleosides, proved to be extremely useful in different antisense strategies, including RNAi. The 2'-O-alkyl modification, carrying an amino functionality, deserves special attention due to its ability to neutralize the negatively charged phosphate backbone, leading to improved physicochemical and pharmaceutical properties of antisense agents. Here, we report a very short, convenient, and straightforward synthesis of phosphoramidites for all four 2'-aminoethyl-modified natural ribonucleosides, where the aminoethyl group is introduced in a single alkylation step.