5'-O-(4,4'-dimethoxytrityl)-2'-N,3'-O-(2-(trichloromethyl)oxazolino)-2'-deoxy-1-(β-D-ribofuranosyl)uracil | 174221-82-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 5'-O-(4,4'-dimethoxytrityl)-2'-N,3'-O-(2-(trichloromethyl)oxazolino)-2'-deoxy-1-(β-D-ribofuranosyl)uracil
• 英文别名: 1-[(3aR,4R,6R,6aS)-6-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-2-(trichloromethyl)-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]oxazol-4-yl]pyrimidine-2,4-dione
• CAS: 174221-82-0
• 化学式: C₃₂H₂₈Cl₃N₃O₇
• 分子量: 672.949
• InChiKey: STGVBEDXESGNMZ-YULOIDQLSA-N

物化性质

• 密度：
  1.46±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  45
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5'-O-(4,4'-dimethoxytrityl)-2'-N,3'-O-(2-(trichloromethyl)oxazolino)-2'-deoxy-1-(β-D-ribofuranosyl)uracil 在 caesium carbonate 作用下， 以 甲醇 、 乙醇 、 水 、 甲苯 为溶剂， 反应 173.0h， 生成 1-{3-[bis(2-hydroxyethyl)amino]-5-[bis(4-methoxyphenyl)phenylmethoxymethyl]-4-hydroxytetrahydrofuran-2-yl}-3-methyl-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Syntheses of Silatranyl- and Germatranyluridines

  摘要：

  [GRAPHICS]Silatranyluridine 1 and germatranyluridine 2 have been prepared in five steps from oxazolinouridine 3 in 27 and 29% yields, respectively. These compounds are novel transition-state analogues (TSAs) for RNA hydrolysis and offer a number of advantages over traditional vanadium-or rhenium-based TSAs. Germatrane 2 is completely stable in D2O at room temperature, and the half-life of silatrane 1 in D2O was found to be > 7 days by H-1 NMR spectroscopy.

  DOI：

  10.1021/ol050133v
• 作为产物：
  描述：

  2,2'-脱水尿苷 在 4-二甲氨基吡啶 、 sodium hydride 作用下， 以 吡啶 为溶剂， 反应 32.0h， 生成 5'-O-(4,4'-dimethoxytrityl)-2'-N,3'-O-(2-(trichloromethyl)oxazolino)-2'-deoxy-1-(β-D-ribofuranosyl)uracil
  参考文献：
  名称：

  2‘-Amino-2‘-deoxyuridine via an Intramolecular Cyclization of a Trichloroacetimidate

  摘要：

  DOI：

  10.1021/jo9510548

文献信息

• Novel nucleosides via intramolecular functionalization of 2,2′-anhydrouridine derivatives
  作者：Danny P.C. McGee、David P. Sebesta、Sarah S. O'Rourke、Rogelio L. Martinez、Michael E. Jung、Wolfgang A. Pieken

  DOI：10.1016/0040-4039(96)00227-4

  日期：1996.3

  The generation of novel ribonucleoside analogues derived from 2,2′-anhydrouridines by a 3′-hydroxyl directed intramolecular nucleophilic substitution of the 2′-position is described. The methodology allows for the efficient, regio- and stereoselective elaboration of the 2′-position, often under exceptionally mild reaction conditions.

  描述了通过2'-位的3'-羟基定向分子内亲核取代衍生自2,2'-脱水尿苷的新型核糖核苷类似物。该方法通常可以在非常温和的反应条件下，对2'-位进行高效，区域和立体选择性修饰。
• 2‘-Amino-2‘-deoxyuridine <i>via </i>an Intramolecular Cyclization of a Trichloroacetimidate
  作者：Danny P. C. McGee、Alecia Vaughn-Settle、Chandra Vargeese、Yansheng Zhai

  DOI：10.1021/jo9510548

  日期：1996.1.1
• Syntheses of Silatranyl- and Germatranyluridines
  作者：Chad M. Rink、Matthew C. Mauck、Irfan Asif、Michael E. Pitzer、Edward E. Fenlon

  DOI：10.1021/ol050133v

  日期：2005.3.1

  [GRAPHICS]Silatranyluridine 1 and germatranyluridine 2 have been prepared in five steps from oxazolinouridine 3 in 27 and 29% yields, respectively. These compounds are novel transition-state analogues (TSAs) for RNA hydrolysis and offer a number of advantages over traditional vanadium-or rhenium-based TSAs. Germatrane 2 is completely stable in D2O at room temperature, and the half-life of silatrane 1 in D2O was found to be > 7 days by H-1 NMR spectroscopy.