(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 | 689221-95-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (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
• 英文别名: (6aR,8R,9R,9aS)-8-(4,6-difluorobenzimidazol-1-yl)-2,2,4,4-tetra(propan-2-yl)-6a,8,9,9a-tetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-9-ol
• CAS: 689221-95-2
• 化学式: C₂₄H₃₈F₂N₂O₅Si₂
• 分子量: 528.744
• InChiKey: DDFMWEOIAPLHPB-MSNJVRRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.53
• 重原子数：
  35
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  75
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  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 4-二甲氨基吡啶 、 锂硼氢 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 生成 Toluene-4-sulfonic acid 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]-ethyl ester
  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'-(4,6-difluoro-1H-benzimidazol-1-yl)-β-D-ribofuranose 在 三乙胺 作用下， 以 吡啶 为溶剂， 生成 (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
  参考文献：
  名称：

  A novel entry to 2′-O-aminopropyl modified nucleosides amenable for further modifications

  摘要：

  2'-O-aminopropyl modified 4,6-difluoro-substituted benzimidazole nucleosides were synthesized in a two-step synthesis via Michael reaction and a Raney-nickel catalyzed reduction in high yields. These building blocks were used as a starting point for the conjugation of different carboxylic acids to enhance the lipophilicity or cationic character of oligonucleotides when used in biological assays or medical applications. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.10.053

文献信息

• A novel entry to 2′-O-aminopropyl modified nucleosides amenable for further modifications
  作者：Jens Haas、Joachim W. Engels

  DOI：10.1016/j.tetlet.2007.10.053

  日期：2007.12

  2'-O-aminopropyl modified 4,6-difluoro-substituted benzimidazole nucleosides were synthesized in a two-step synthesis via Michael reaction and a Raney-nickel catalyzed reduction in high yields. These building blocks were used as a starting point for the conjugation of different carboxylic acids to enhance the lipophilicity or cationic character of oligonucleotides when used in biological assays or medical applications. (C) 2007 Elsevier Ltd. All rights reserved.
• The Effect of Universal Fluorinated Nucleobases on the Catalytic Activity of Ribozymes
  作者：A. E. Klöpffer、J. W. Engels

  DOI：10.1081/ncn-120022962

  日期：2003.10

  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.