5'-O-tert-butyldimethylsilyl-6-(1,3-diphenylimidazolidin-2-yl)-2',3'-O-isopropylideneuridine | 325705-76-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 5'-O-tert-butyldimethylsilyl-6-(1,3-diphenylimidazolidin-2-yl)-2',3'-O-isopropylideneuridine
• 英文别名: 1-[(3aR,4R,6R,6aR)-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-6-(1,3-diphenylimidazolidin-2-yl)pyrimidine-2,4-dione
• CAS: 325705-76-8
• 化学式: C₃₃H₄₄N₄O₆Si
• 分子量: 620.821
• InChiKey: YPZPNZOBDODCGC-MZAPLOMJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.0
• 重原子数：
  44
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  92.8
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5'-O-tert-butyldimethylsilyl-6-(1,3-diphenylimidazolidin-2-yl)-2',3'-O-isopropylideneuridine 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 36.0h， 以94%的产率得到6-(1,3-diphenylimidazolidin-2-yl)-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
• 作为产物：
  描述：

  5'-O-(t-butyldimethylsilyl)-2',3'-O-isopropylideneuridine 在 溶剂黄146 、 lithium diisopropyl amide 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 72.0h， 生成 5'-O-tert-butyldimethylsilyl-6-(1,3-diphenylimidazolidin-2-yl)-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

• The 5′,6-Oxomethylene Transglycosidic Tether for Conformational Restriction of Pyrimidine Ribonucleosides. Investigation of 6-Formyl- and 6-(Hydroxymethyl)uridine 5′-Carboxaldehydes
  作者：Michael P. Groziak、Ronghui Lin

  DOI：10.1016/s0040-4020(00)00970-4

  日期：2000.12

  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.