2',3',5'-tri-O-(4-methylbenzoyl)adenosine | 863591-90-6

• 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',3',5'-tri-O-(4-methylbenzoyl)adenosine
• 英文别名: Bz(4-Me)(-2)[Bz(4-Me)(-3)][Bz(4-Me)(-5)]Ribf(b)-adenin-9-yl；[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-3,4-bis[(4-methylbenzoyl)oxy]oxolan-2-yl]methyl 4-methylbenzoate
• CAS: 863591-90-6
• 化学式: C₃₄H₃₁N₅O₇
• 分子量: 621.649
• InChiKey: GVVOEQKMHKDTGE-QWOIFIOOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  46
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  158
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2',3',5'-tri-O-(4-methylbenzoyl)adenosine 在 双氧水 、 溶剂黄146 作用下， 反应 12.0h， 以93%的产率得到2',3',5'-tri-O-(4-methybenzoyl)adenosine 1-oxide
  参考文献：
  名称：

  腺苷型核苷的N-氧化物经过嘧啶环的打开和闭合，生成5-氨基-4-（1,2,4-恶二唑-3-基）咪唑衍生物。

  摘要：

  用羧酸酐和苯硫酚处理酰化的腺苷N-氧化物导致嘧啶开环，然后闭环。氨解产生5-氨基-4-（5-取代的1,2,4-恶二唑-3-基）-1-（β-d-呋喃呋喃糖基）咪唑衍生物，而甲醇中的碘选择性地掩盖了5-氨基。相关的柔性核苷类似物可以从腺嘌呤型前体制备。

  DOI：

  10.1021/ol061715v
• 作为产物：
  描述：

  腺苷 在 吡啶 作用下， 以 甲醇 为溶剂， 反应 14.0h， 生成 2',3',5'-tri-O-(4-methylbenzoyl)adenosine
  参考文献：
  名称：

  Nucleic Acid Related Compounds. 127. Selective N-Deacylation of N,O-Peracylated Nucleosides in Superheated Methanol¹

  摘要：

  Solutions of peracylated adenosine, cytidine, and related nucleoside derivatives undergo selective N-deacylation upon heating at elevated temperatures (oil bath >= 105 degrees C) in methanol. An increase in the bulk of the N-acyl group has little effect on the rate of N-deacylation but increases the N/O selectivity ratio. Extended heating is required for N-deacylation with arylcarboxylic acid derivatives. Contamination with acidic or basic reagent residues is avoided.

  DOI：

  10.1021/jo051256w

文献信息

• Selective Removal of the 2‘- and 3‘-<i>O</i>-Acyl Groups from 2‘,3‘,5‘-Tri-<i>O</i>-acylribonucleoside Derivatives with Lithium Trifluoroethoxide¹
  作者：Ireneusz Nowak、Carl T. Jones、Morris J. Robins

  DOI：10.1021/jo0600104

  日期：2006.4.1

  Selective cleavage of O2' and O3' ester groups from ribonucleoside derivatives has been accomplished with Dowex 1 x 2 (CF3CH2O-) in 2,2,2-trifluoroethanol (TFE) or lithium trifluoroethoxide/TFE. Deacylations with Li+ -OCH2CF3/TFE proceed at ambient temperature (or with mild heating) to give the 5'-O-acyl derivatives in superior yields and higher purity than prior approaches for selective O2' and O3' ester deprotection.
• Oligonucleotide Synthesis Involving Deprotection of Amidine-Type Protecting Groups for Nucleobases under Acidic Conditions
  作者：Akihiro Ohkubo、Yasukazu Kuwayama、Yudai Nishino、Hirosuke Tsunoda、Kohji Seio、Mitsuo Sekine

  DOI：10.1021/ol100676j

  日期：2010.6.4

  Amidine-type protecting groups, i.e., N,N-dimethylformamidine (dmf) and N,N-dibutylformamidine (dbf) groups, introduced Into nucleobases were rapidly removed under mild acidic conditions using imidazolium triflate (IMT) or 1-hydroxybenztriazole (HOBt). This new deprotection strategy allowed a 2'-O-methyl-RNA derivative bearing a base-labile group to be efficiently synthesized using a silyl-type linker. It was also found that our new method could be applied to the synthesis of an unmodified RNA oligomer.
• Nucleic Acid Related Compounds. 127. Selective N-Deacylation of N,O-Peracylated Nucleosides in Superheated Methanol¹
  作者：Ireneusz Nowak、Martin Conda-Sheridan、Morris J. Robins

  DOI：10.1021/jo051256w

  日期：2005.9.1

  Solutions of peracylated adenosine, cytidine, and related nucleoside derivatives undergo selective N-deacylation upon heating at elevated temperatures (oil bath >= 105 degrees C) in methanol. An increase in the bulk of the N-acyl group has little effect on the rate of N-deacylation but increases the N/O selectivity ratio. Extended heating is required for N-deacylation with arylcarboxylic acid derivatives. Contamination with acidic or basic reagent residues is avoided.
• <i>N</i>-Oxides of Adenosine-Type Nucleosides Undergo Pyrimidine Ring Opening and Closure To Give 5-Amino-4-(1,2,4-oxadiazol-3-yl)imidazole Derivatives
  作者：Ireneusz Nowak、John F. Cannon、Morris J. Robins

  DOI：10.1021/ol061715v

  日期：2006.9.1

  Treatment of acylated adenosine N-oxides with carboxylic anhydrides and thiophenol resulted in pyrimidine ring opening followed by exocyclic ring closure. Ammonolysis gave 5-amino-4-(5-substituted-1,2,4-oxadiazol-3-yl)-1-(beta-d-ribofuranosyl)imidazole derivatives, whereas iodine in methanol selectively unmasked the 5-amino group. Related flexible nucleoside analogues can be prepared from adenine-type

  用羧酸酐和苯硫酚处理酰化的腺苷N-氧化物导致嘧啶开环，然后闭环。氨解产生5-氨基-4-（5-取代的1,2,4-恶二唑-3-基）-1-（β-d-呋喃呋喃糖基）咪唑衍生物，而甲醇中的碘选择性地掩盖了5-氨基。相关的柔性核苷类似物可以从腺嘌呤型前体制备。