(6R,5'S)-6,5':7,5'-dianhydro-5,6-dihydro-6,5'-dihydroxy-6-hydroxymethyl-2',3'-O-isopropylideneuridine | 325705-82-6

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (6R,5'S)-6,5':7,5'-dianhydro-5,6-dihydro-6,5'-dihydroxy-6-hydroxymethyl-2',3'-O-isopropylideneuridine
• 英文别名: (1S,2R,5R,11R,12R,16S)-14,14-dimethyl-3,13,15,17,18-pentaoxa-8,10-diazapentacyclo[9.5.1.12,5.05,10.012,16]octadecane-7,9-dione
• CAS: 325705-82-6
• 化学式: C₁₃H₁₆N₂O₇
• 分子量: 312.279
• InChiKey: HQBJKBYHXJFIHJ-XPUCRGHOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  95.6
• 氢给体数：
  1
• 氢受体数：
  7

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-2',3'-O-isopropylideneuridine 在 吡啶 、 三氟乙酸 作用下， 反应 54.5h， 生成 2',3',5'-tri-O-acetyl-5',6-(oxomethylene)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
• 作为产物：
  描述：

  5'-O-[(tert-butyl)dimethylsilyl]-6-{[(tert-butyl)diphenylsilyloxy]methyl}-2',3'-O-isopropylideneuridine 在 四丁基氟化铵 、 4-甲基苯磺酸吡啶 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 28.0h， 生成 (6R,5'S)-6,5':7,5'-dianhydro-5,6-dihydro-6,5'-dihydroxy-6-hydroxymethyl-2',3'-O-isopropylideneuridine
  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.