(6R,5'S)-6,5':7,5'-dianhydro-5,6-dihydro-6,5'-dihydroxy-6-(hydroxymethyl)uridine | 325705-83-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (6R,5'S)-6,5':7,5'-dianhydro-5,6-dihydro-6,5'-dihydroxy-6-(hydroxymethyl)uridine
• CAS: 325705-83-7
• 化学式: C₁₀H₁₂N₂O₇
• 分子量: 272.214
• InChiKey: CTCIFXAIEAUDFE-HBFZMRAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.54
• 重原子数：
  19.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  117.56
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (6R,5'S)-6,5':7,5'-dianhydro-5,6-dihydro-6,5'-dihydroxy-6-(hydroxymethyl)uridine 在 吡啶 、 potassium cyanide 作用下， 以 氘代甲醇 为溶剂， 反应 21.5h， 生成
  参考文献：
  名称：

  The 5′,6-Oxomethylene Transglycosidic Tether for Conformational Restriction of Pyrimidine Ribonucleosides. Investigation of 6-Formyl- and 6-(Hydroxymethyl)uridine 5′-Carboxaldehydes

  摘要：

  In an effort to develop a new motif for the transglycosidic tethering of the pyrimidine nucleoside framework, the 2',3'-O-isopropylidenated and unprotected versions of 6-formyl- and 6-(hydroxymethyl)uridine 5'-carboxaldehyde were prepared and these were examined for their ability to adopt 5',6-oxomethylene tethered solution structures. In aqueous solution, the 2',3'-O-isopropylidenated nucleosides readily generated spiro-dihydrouridines via proximity-induced transglycosidic intramolecular reactions. In stark contrast, their unprotected counterparts existed mainly as the untethered aldehyde hydrates. Based on these findings, the 5',6-oxomethylene transglycosidic tether appears to constitute a useful conformational restriction motif for the pyrimidine ribonucleoside flamework, but only when the 5'-OH group is functionalized. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00970-4
• 作为产物：
  描述：

  6-[(tert-butyldiphenylsilyloxy)methyl]-2',3'-O-isopropylideneuridine 5'-carboxaldehyde 在 四丁基氟化铵 、 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 生成 (6R,5'S)-6,5':7,5'-dianhydro-5,6-dihydro-6,5'-dihydroxy-6-(hydroxymethyl)uridine
  参考文献：
  名称：

  The 5′,6-Oxomethylene Transglycosidic Tether for Conformational Restriction of Pyrimidine Ribonucleosides. Investigation of 6-Formyl- and 6-(Hydroxymethyl)uridine 5′-Carboxaldehydes

  摘要：

  In an effort to develop a new motif for the transglycosidic tethering of the pyrimidine nucleoside framework, the 2',3'-O-isopropylidenated and unprotected versions of 6-formyl- and 6-(hydroxymethyl)uridine 5'-carboxaldehyde were prepared and these were examined for their ability to adopt 5',6-oxomethylene tethered solution structures. In aqueous solution, the 2',3'-O-isopropylidenated nucleosides readily generated spiro-dihydrouridines via proximity-induced transglycosidic intramolecular reactions. In stark contrast, their unprotected counterparts existed mainly as the untethered aldehyde hydrates. Based on these findings, the 5',6-oxomethylene transglycosidic tether appears to constitute a useful conformational restriction motif for the pyrimidine ribonucleoside flamework, but only when the 5'-OH group is functionalized. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00970-4

文献信息

• Development of Novel Bridged and Caged Nucleoside Analogs as Biochemical Tools
  作者：Michael P. Groziak、Ronghui Lin

  DOI：10.1080/07328319708006196

  日期：1997.7

  New classes of closely biomimetic, anti conformation restricted, transglycosidic spiro, bridged, and caged pyrimidine nucleoside analogs are being developed. Progress towards accessing members of the new caged 2'-deoxyuridine mimic class is related.