2',3',5'-tri-O-(4-methylbenzoyl)uridine | 81777-53-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 2',3',5'-tri-O-(4-methylbenzoyl)uridine
• 英文别名: 2',3',5'-tri-O-p-toluyluridine；1-(3,4,6-tri-O-p-toluyl-1-deoxy-β-D-psicofuranosyl)-uracil；O^2'_,O3'_,O5'-tris-(4-methyl-benzoyl)-uridine；Bz(4-Me)(-2)[Bz(4-Me)(-3)][Bz(4-Me)(-5)]Ribf(b)-uracil-1-yl；[(2R,3R,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-bis[(4-methylbenzoyl)oxy]oxolan-2-yl]methyl 4-methylbenzoate
• CAS: 81777-53-9
• 化学式: C₃₃H₃₀N₂O₉
• 分子量: 598.609
• InChiKey: NXOJCESGNUDUNM-YXINZVNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  44
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  138
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2',3',5'-tri-O-(4-methylbenzoyl)uridine 在 一氯化碘 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以96%的产率得到5-Iodo-2',3',5'-tri-O-p-toluyluridine
  参考文献：
  名称：

  核酸相关化合物。38. 尿嘧啶碱基和对甲苯甲酰保护的核苷的 C-5 处的顺利和高产碘化和氯化

  摘要：

  用一氯化碘 (ICl) 处理尿嘧啶碱基和受保护的核苷，得到相应的 5-碘尿嘧啶产物，纯化产率超过 95%。用二氯化碘苯 (PhICl2) 进行类似的简便氯化。将核苷保护为对甲苯基酯提供了可溶于有机溶剂并容易以高产率结晶的反应物。

  DOI：

  10.1139/v82-082
• 作为产物：
  描述：

  胞苷 在 吡啶 、 水 作用下， 以 乙二醇二甲醚 为溶剂， 反应 15.0h， 生成 2',3',5'-tri-O-(4-methylbenzoyl)uridine
  参考文献：
  名称：

  Hydrothermal Deamidation of 4-N-Acylcytosine Nucleoside Derivatives:  Efficient Synthesis of Uracil Nucleoside Esters

  摘要：

  [GRAPHICS]N,O-Peracylated cytidine and 2'-deoxycytidine derivatives in superheated water/DME solutions (oil bath at 125 degrees C) undergo hydrolytic deamidation (and/or N-deacylation). Acylated starting materials derived from arylcarboxylic acids give the corresponding uridine esters cleanly, and such derivatives crystallize selectively from the cooled reaction mixtures in high yields.

  DOI：

  10.1021/ol0518378

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.
• Hydrothermal Deamidation of 4-<i>N</i>-Acylcytosine Nucleoside Derivatives:  Efficient Synthesis of Uracil Nucleoside Esters
  作者：Ireneusz Nowak、Morris J. Robins

  DOI：10.1021/ol0518378

  日期：2005.10.1

  [GRAPHICS]N,O-Peracylated cytidine and 2'-deoxycytidine derivatives in superheated water/DME solutions (oil bath at 125 degrees C) undergo hydrolytic deamidation (and/or N-deacylation). Acylated starting materials derived from arylcarboxylic acids give the corresponding uridine esters cleanly, and such derivatives crystallize selectively from the cooled reaction mixtures in high yields.
• Nucleic acid related compounds. 38. Smooth and high-yield iodination and chlorination at C-5 of uracil bases and <i>p</i>-toluyl-protected nucleosides
  作者：Morris J. Robins、Philip J. Barr、Jerzy Giziewicz

  DOI：10.1139/v82-082

  日期：1982.3.1

  Treatment of uracil bases and protected nucleosides with iodine monochloride (ICl) gave the corresponding 5-iodouracil products in over 95% purified yields. Analogously facile chlorination was effected with iodobenzene dichloride (PhICl2). Protection of the nucleosides as p-toluyl esters provided reactants that were soluble in organic solvents and crystallized readily in high yields.

  用一氯化碘 (ICl) 处理尿嘧啶碱基和受保护的核苷，得到相应的 5-碘尿嘧啶产物，纯化产率超过 95%。用二氯化碘苯 (PhICl2) 进行类似的简便氯化。将核苷保护为对甲苯基酯提供了可溶于有机溶剂并容易以高产率结晶的反应物。