1-[2,5-O-bis(tert-butyldimethylsilyl)-3-O-phenylthiocarbonyl-β-D-pentofuranosyl]-uracyl | 161110-04-9

• 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: 1-[2,5-O-bis(tert-butyldimethylsilyl)-3-O-phenylthiocarbonyl-β-D-pentofuranosyl]-uracyl
• 英文别名: 2',5'-Bis-O-(tert-butyldimethylsilyl)-3'-O-(phenoxythiocarbonyl)uridine；1-[(2R,3R,4R,5R)-3-[tert-butyl(dimethyl)silyl]oxy-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-phenoxycarbothioyloxyoxolan-2-yl]pyrimidine-2,4-dione
• CAS: 161110-04-9
• 化学式: C₂₈H₄₄N₂O₇SSi₂
• 分子量: 608.904
• InChiKey: DMPRVBBOVWPODE-MSNJVRRCSA-N

物化性质

• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  40
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  128
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-[2,5-O-bis(tert-butyldimethylsilyl)-3-O-phenylthiocarbonyl-β-D-pentofuranosyl]-uracyl 在 偶氮二异丁腈 、 三苯基氢化锡 作用下， 以 甲苯 为溶剂， 反应 23.0h， 以98%的产率得到2',5'-Bis-O-(tert-butyldimethylsilyl)-3'-deoxyuridine
  参考文献：
  名称：

  A Synthesis of 5′-Amino-3′,5′-dideoxyuridine

  摘要：

  介绍了从尿苷开始合成3',5'-二脱氧-5'-氨基尿苷的过程。

  DOI：

  10.1055/s-2000-6346
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 在 4-二甲氨基吡啶 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 反应 22.0h， 生成 1-[2,5-O-bis(tert-butyldimethylsilyl)-3-O-phenylthiocarbonyl-β-D-pentofuranosyl]-uracyl
  参考文献：
  名称：

  Nucleosides. LVI¹Synthesis and Chemical Modifications of 3′-Deoxy-Pyrimidine Nucleosides

  摘要：

  3'-Deoxyuridine(1) and 3'-deoxycytidine(2) were prepared with improved yields by two different methods applying either the Barton procedure to appropriate 2',5'-di-O-protected pyrimidine nucleosides or by choosing the direct glycosylation of the pyrimidine bases with 1,2-di-O-acetyl-5-O-toluoyl-3-deoxy-D-erythro-pentofuranose via the silylation approach. Suitable protecting groups for the sugar moiety have been found in the trityl, tert-butyldimethylsilyl and the thexyl groups which are inert in the radical deoxygenation process. The newly synthesised compounds were characterised by elemental analyses and UV and H-1-NMR spectra.

  DOI：

  10.1080/15257779408012162

文献信息

• Synthesis and Properties of RNA Analogues Having Amides as Interuridine Linkages at Selected Positions
  作者：Eriks Rozners、Dace Katkevica、Erika Bizdena、Roger Strömberg

  DOI：10.1021/ja0360900

  日期：2003.10.1

  oligonucleotides and RNA had stability similar to unmodified RNA-RNA duplexes (Delta t(m)= -0.2 to +0.7 degrees C per modification). However, the AM2 modification resulted in substantial stabilization of duplexes: Delta t(m)= +1 to +2.4 degrees C per modification compared to all RNA. A 2'-O-methyl vicinal to the AM2 linkage further increased the duplex stability. Our results suggest that RNA analogues having

  已合成在选定位置具有酰胺核苷间键（AM1：3'-CH(2)CONH-5' 和 AM2：3'-CH(2)NHCO-5'）的寡核糖核苷酸类似物，并且由这些形成的双链体的热稳定性已通过 UV 熔解实验评估了具有互补 RNA 片段的类似物。研究了两个系列的具有 2'-OH 或 2'-OMe 邻近酰胺键的低聚物。单体合成子（3' 和 5'-C 胺和羧酸）合成如下： 对于 AM1 类似物的合成，采用已知的自由基烯丙基化序列，然后是双键断裂。为了合成 AM2 类似物，开发了通过添加硝基甲烷然后将硝基官能团转化为氨基或羧基的新途径。单体胺和羧酸偶联，然后进行保护基操作和膦酰化，得到用于寡核苷酸合成的二聚体 3'-膦酸结构单元。还制备了具有 3'-酰胺和 2'-OH 或 2'-OMe 基团的单体模型化合物，并通过 (1) H NMR 确定了它们的构象平衡。AM1 和 AM2 模型对北方构象异构体表现出相同的偏好（在
• Synthesis and Properties of Oligoribonucleotide Analogues Having Amide (3″-CH₂-CO-NH-5′) Internucleoside Linkages
  作者：Eriks Rozners、Roger Strömberg

  DOI：10.1080/07328319708006117

  日期：1997.7

  Amide linked ribonucleoside dimer 5 was prepared and converted into selectively protected H-phosphonate building block 9. Oligoribonucleotide duplexes having amide linkages at selected sites were synthesized and their stability was studied by UV melting experiments.
• A Synthesis of 5′-Amino-3′,5′-dideoxyuridine
  作者：David M. Bender、D. David Hennings、Robert M. Williams

  DOI：10.1055/s-2000-6346

  日期：——

  The synthesis of 3′,5′-dideoxy-5′-aminouridine starting from uridine is described.

  介绍了从尿苷开始合成3',5'-二脱氧-5'-氨基尿苷的过程。
• Nucleosides. LVI¹Synthesis and Chemical Modifications of 3′-Deoxy-Pyrimidine Nucleosides
  作者：Soo-Young Rhie、Wolfgang Pfleiderer

  DOI：10.1080/15257779408012162

  日期：1994.7

  3'-Deoxyuridine(1) and 3'-deoxycytidine(2) were prepared with improved yields by two different methods applying either the Barton procedure to appropriate 2',5'-di-O-protected pyrimidine nucleosides or by choosing the direct glycosylation of the pyrimidine bases with 1,2-di-O-acetyl-5-O-toluoyl-3-deoxy-D-erythro-pentofuranose via the silylation approach. Suitable protecting groups for the sugar moiety have been found in the trityl, tert-butyldimethylsilyl and the thexyl groups which are inert in the radical deoxygenation process. The newly synthesised compounds were characterised by elemental analyses and UV and H-1-NMR spectra.