N6-benzoyl-2′-O-[acetal levulinic ester]-3′,5′-O-[1,1,3,3-tetrakis-(1-methylethyl)-1,3-disiloxanediyl]-adenosine | 1541908-21-7

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: N6-benzoyl-2′-O-[acetal levulinic ester]-3′,5′-O-[1,1,3,3-tetrakis-(1-methylethyl)-1,3-disiloxanediyl]-adenosine
• 英文别名: N⁶-benzoyl-2′-O-[acetal levulinic ester]-3′,5′-O-[1,1,3,3-tetrakis-(1-methylethyl)-1,3-disiloxanediyl]-adenosine
• CAS: 1541908-21-7
• 化学式: C₃₅H₅₁N₅O₉Si₂
• 分子量: 741.989
• InChiKey: XMIVOJAODPLSQZ-PLXIXOFTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.19
• 重原子数：
  51.0
• 可旋转键数：
  13.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  162.22
• 氢给体数：
  1.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  N6-benzoyl-2′-O-[acetal levulinic ester]-3′,5′-O-[1,1,3,3-tetrakis-(1-methylethyl)-1,3-disiloxanediyl]-adenosine 在 吡啶 、 silver nitrate 、 triethylamine tris(hydrogen fluoride) 作用下， 以 四氢呋喃 为溶剂， 反应 3.7h， 生成 N6-benzoyl-2′-O-[acetal levulinic ester]-5′-O-[4,4′-dimethoxytrityl]-adenosine
  参考文献：
  名称：

  Regiospecific Solid-Phase Synthesis of Branched Oligoribonucleotides That Mimic Intronic Lariat RNA Intermediates

  摘要：

  We have developed new solid phase methods for the synthesis of branched RNAs that mimic intronic lariat RNA intermediates. These methods produce branched oligoribonucleotide sequences of arbitrary length, base composition, and regiochemistry at the branchpoint junction. The methods utilize branching monomers that allow for the growth of each branch regioselectively from any of the hydroxyl positions (5', 3', or 2') at the branch-point junction. The integrity and branchpoint connectivity of the synthetic products have been confirmed by HPLC and MS analysis, and cleavage of the 2',5' linkage by recombinant debranching enzyme. Nonhydrolyzable branched RNA analogues containing arabinose instead of ribose at the branchpoint junction were shown to inhibit debranching activity and, hence, represent "decoys" for sequestering RNA binding proteins thought to drive amyotrophic lateral sclerosis (ALS).

  DOI：

  10.1021/jo4024182
• 作为产物：
  描述：

  5-氧代己酸 、 N⁶-benzoyl-2'-O-methylthiomethyl-5',3'-O-(1,1,3,3-tetraisopropyldisiloxan-1,3-diyl)adenosine 在 cesium bicarbonate 、 磺酰氯 作用下， 以 N,N-二甲基甲酰胺 、 二氯甲烷 为溶剂， 反应 21.0h， 以59%的产率得到N6-benzoyl-2′-O-[acetal levulinic ester]-3′,5′-O-[1,1,3,3-tetrakis-(1-methylethyl)-1,3-disiloxanediyl]-adenosine
  参考文献：
  名称：

  Regiospecific Solid-Phase Synthesis of Branched Oligoribonucleotides That Mimic Intronic Lariat RNA Intermediates

  摘要：

  We have developed new solid phase methods for the synthesis of branched RNAs that mimic intronic lariat RNA intermediates. These methods produce branched oligoribonucleotide sequences of arbitrary length, base composition, and regiochemistry at the branchpoint junction. The methods utilize branching monomers that allow for the growth of each branch regioselectively from any of the hydroxyl positions (5', 3', or 2') at the branch-point junction. The integrity and branchpoint connectivity of the synthetic products have been confirmed by HPLC and MS analysis, and cleavage of the 2',5' linkage by recombinant debranching enzyme. Nonhydrolyzable branched RNA analogues containing arabinose instead of ribose at the branchpoint junction were shown to inhibit debranching activity and, hence, represent "decoys" for sequestering RNA binding proteins thought to drive amyotrophic lateral sclerosis (ALS).

  DOI：

  10.1021/jo4024182