2'-脱氧-3',5'-二-O-(4-甲基苯甲酰)尿苷 | 4449-38-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 中文名称: 2'-脱氧-3',5'-二-O-(4-甲基苯甲酰)尿苷
• 英文名称: 2'-deoxy-3',5'-di-O-(4-methylbenzoyl)uridine
• 英文别名: 3',5'-di-O-p-toluyl-2'-deoxyuridine；2'-deoxy-3',5'-bis-O-(4-toluoyl)uridine；2'-deoxy-3',5'-di-O-4-toluoyluridine；3',5'-Di-O-p-toluoyl-2'-desoxy-β-uridin；O^3'_,O5'-bis-(4-methyl-benzoyl)-2'-deoxy-uridine；3',5'-Di-O-p-toluyl-2'-desoxy-uridin；2'-Deoxy-3',5'-DI-O-(4-methylbenzoyl)-uridine；[(2R,3S,5R)-5-(2,4-dioxopyrimidin-1-yl)-3-(4-methylbenzoyl)oxyoxolan-2-yl]methyl 4-methylbenzoate
• CAS: 4449-38-1
• 化学式: C₂₅H₂₄N₂O₇
• 分子量: 464.475
• InChiKey: PHIPERUMORAWER-TUNNFDKTSA-N

物化性质

• 溶解度：
  溶于丙酮、氯仿、二甲亚砜

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2'-脱氧-3',5'-二-O-(4-甲基苯甲酰)尿苷 在 一氯化碘 作用下， 以 二氯甲烷 为溶剂， 以91%的产率得到5-iodo-3',5'-di-O-p-toluyl-2'-deoxyuridine
  参考文献：
  名称：

  Synthesis of Carbohydrate-Conjugated dT Analogues Using ‘Click Chemistry’

  摘要：

  一种新型呋喃[2,3-d]嘧啶核苷与多种碳水化合物的偶联物，通过Sonogashira偶联和‘点击化学’合成。随后，在甲醇中用催化量的甲醇钠脱除4-甲苯酰基和乙酰基的保护，呋喃[2,3-d]嘧啶发生了重排，变成开环的酮型结构。其结构通过光谱学得以确认。

  DOI：

  10.1055/s-2007-983881
• 作为产物：
  描述：

  2'-脱氧胞苷盐酸盐 在 吡啶 、 水 作用下， 以 乙二醇二甲醚 为溶剂， 反应 15.0h， 生成 2'-脱氧-3',5'-二-O-(4-甲基苯甲酰)尿苷
  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

• 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。
• A General Route to 4-C-Substituted Pyrimidine Nucleosides
  作者：Thomas Carell、Ulrich Hennecke、David Kuch

  DOI：10.1055/s-2007-965935

  日期：2007.3

  Palladium-catalyzed cross-coupling reactions of tin and zinc nucleophiles with arylsulfonates of pyrimidine nucleosides have been achieved to give a wide range of 4-C-substituted pyrimidine nucleosides. This method also allows the construction of pyrimidine-pyrimidinone dinucleosides, containing the carbon skeleton of the (6-4) DNA photo lesion.

  在钯催化下，锡和锌亲核物与嘧啶核苷的芳基磺酸盐发生了交叉偶联反应，生成了多种 4-C 取代的嘧啶核苷。这种方法还可以构建含有 (6-4) DNA 光变碳骨架的嘧啶-嘧啶酮二核苷。
• Synthesis, Conformation and Biological Properties of Selenonucleosides
  作者：Krzysztof Felczak、Agnieszka Miazga、Barbara Golos、Wojciech Rode、David Shugar、Tadeusz Kulikowski

  DOI：10.1080/15257779908041523

  日期：1999.4

  Synthesis, conformation and antitumour properties of novel 2- and 4-selenopyrimidine nucleosides are described.
• Investigation of stereoselectivities in the coupling reactions of 1-O-methyl-3, 5-di-O-p-toluoyl-2-deoxyribofuranoside with purines and pyrimidines
  作者：Selvasekaran Janardhanam、Krishnan P. Nambiar

  DOI：10.1016/s0040-4039(00)73064-4

  日期：1994.5

  Stereoselectivities in the coupling reaction between 1-O-methyl-3,5-di-O-p-toluoyl-2-deoxyribofuranoside and suitably protected purine and pyrimidine derivatives have been examined in acetonitrile with varying equivalents of SnCl4. The best result in alpha-nucleoside formation was obtained when the coupling reaction was carried out in the presence of ten equivalents of SnCl4.
• FRESKOS, JOHN N., NUCLEOSIDES AND NUCLEOTIDES, 8,(1989) N, C. 549-555
  作者：FRESKOS, JOHN N.

  DOI：——

  日期：——