(2S,3S,3aS,9aR)-2-(2,4-Difluoro-phenyl)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-ol | 689221-94-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,3S,3aS,9aR)-2-(2,4-Difluoro-phenyl)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-ol
• CAS: 689221-94-1
• 化学式: C₂₃H₃₈F₂O₅Si₂
• 分子量: 488.72
• InChiKey: XVGNEPYSPNVTQZ-WZYRSQIMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.72
• 重原子数：
  32.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  57.15
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2S,3S,3aS,9aR)-2-(2,4-Difluoro-phenyl)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-ol 在 4-二甲氨基吡啶 、 锂硼氢 、 sodium azide 、 sodium hydride 、 三乙胺 、 tin(ll) chloride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-[(2S,3S,3aR,9aR)-2-(2,4-Difluoro-phenyl)-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：

  1,3二氯-1,1,3,3-四异丙基二硅氧烷 、 1-deoxy-1-(2,4-difluorophenyl)-β-D-ribofuranose 在 吡啶 作用下， 以54%的产率得到(2S,3S,3aS,9aR)-2-(2,4-Difluoro-phenyl)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-ol
  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