2-[(2R,3R,3aR,9aR)-2-(4,6-Difluoro-benzoimidazol-1-yl)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-yloxy]-ethanol | 689221-99-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-[(2R,3R,3aR,9aR)-2-(4,6-Difluoro-benzoimidazol-1-yl)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-yloxy]-ethanol
• CAS: 689221-99-6
• 化学式: C₂₆H₄₂F₂N₂O₆Si₂
• 分子量: 572.797
• InChiKey: KUCTYTIPZVNENZ-VNSJUHMKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.55
• 重原子数：
  38.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  84.2
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  2-[(2R,3R,3aR,9aR)-2-(4,6-Difluoro-benzoimidazol-1-yl)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-yloxy]-ethanol 在 4-二甲氨基吡啶 、 sodium azide 、 三乙胺 、 tin(ll) chloride 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-[(2R,3R,3aR,9aR)-2-(4,6-Difluoro-benzoimidazol-1-yl)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-yloxy]-ethylamine
  参考文献：
  名称：

  The Effect of Universal Fluorinated Nucleobases on the Catalytic Activity of Ribozymes

  摘要：

  Four fluoro modified universal nucleobases have been synthesized. The universal nucleobases 1 and 2, containing a 2,4-difluorobenzene as nucleobase and a 4,6-difluorobenzimidazole, respectively, were chemically incorporated into a selected hammerhead ribozyme sequence which has already been retrovirally expressed as an anti-HIV ribozyme to investigate their effect on the catalytic activity of the ribozymes. The substitution of the natural nucleosides with either 1 or 2 results only in a small decrease of the catalytic activity. The K-m value for the monosubstituted ribozyme with a 2,4-difluorobenzene is 309 nM(-1), the corresponding k(cat) is 2.91 (.) 10(-3) min(-1). A disubstituted hammerhead ribozyme carrying one of each modification has also been synthesized. For a further stabilization of the ribozyme/substrate complex 2'-(beta-aminoethoxy) modified fluorinated nucleosides 15 and 16 have been developed.

  DOI：

  10.1081/ncn-120022962
• 作为产物：
  描述：

  (2R,3R,3aS,9aR)-2-(4,6-Difluoro-benzoimidazol-1-yl)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-ol 在 锂硼氢 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 2-[(2R,3R,3aR,9aR)-2-(4,6-Difluoro-benzoimidazol-1-yl)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-yloxy]-ethanol
  参考文献：
  名称：

  The Effect of Universal Fluorinated Nucleobases on the Catalytic Activity of Ribozymes

  摘要：

  Four fluoro modified universal nucleobases have been synthesized. The universal nucleobases 1 and 2, containing a 2,4-difluorobenzene as nucleobase and a 4,6-difluorobenzimidazole, respectively, were chemically incorporated into a selected hammerhead ribozyme sequence which has already been retrovirally expressed as an anti-HIV ribozyme to investigate their effect on the catalytic activity of the ribozymes. The substitution of the natural nucleosides with either 1 or 2 results only in a small decrease of the catalytic activity. The K-m value for the monosubstituted ribozyme with a 2,4-difluorobenzene is 309 nM(-1), the corresponding k(cat) is 2.91 (.) 10(-3) min(-1). A disubstituted hammerhead ribozyme carrying one of each modification has also been synthesized. For a further stabilization of the ribozyme/substrate complex 2'-(beta-aminoethoxy) modified fluorinated nucleosides 15 and 16 have been developed.

  DOI：

  10.1081/ncn-120022962