2'-O-acetyloxymethyl-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)uridine | 910028-84-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2'-O-acetyloxymethyl-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)uridine
• 英文别名: [(6aR,8R,9R,9aR)-8-(2,4-dioxopyrimidin-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-yl]oxymethyl acetate
• CAS: 910028-84-1
• 化学式: C₂₄H₄₂N₂O₉Si₂
• 分子量: 558.776
• InChiKey: KIFNJOBHXKDRGB-JMJGKCIBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  37
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  122
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2'-O-acetyloxymethyl-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)uridine 在 吡啶 、 triethylamine tris(hydrogen fluoride) 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 2'-O-acetyloxymethyl-5'-O-(4,4'-dimethoxytrityl)uridine
  参考文献：
  名称：

  First Evaluation of Acyloxymethyl or Acylthiomethyl Groups as Biolabile 2‘-O-Protections of RNA

  摘要：

  Short oligo-U sequences containing 2'-O-acyloxymethyl or acylthiomethyl groups as biolabile 2'-O-protections of RNA have been synthesized. These modified homouridylates are deprotected upon cellular esterase activation to release the parent RNA. They exhibit exceptional resistance to nuclease degradation, and the evaluation of their pairing properties shows that the 2'-acyloxymethyl groups do not prevent the duplex dsRNA formation. These biolabile 2'-modifications overcome the first hurdle to turn oligoribonucleotides into canditates for RNA interference drugs.

  DOI：

  10.1021/ol0616182
• 作为产物：
  描述：

  2'-O-methylthiomethyl-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine 在 磺酰氯 、 18-冠醚-6 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 2'-O-acetyloxymethyl-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)uridine
  参考文献：
  名称：

  First Evaluation of Acyloxymethyl or Acylthiomethyl Groups as Biolabile 2‘-O-Protections of RNA

  摘要：

  Short oligo-U sequences containing 2'-O-acyloxymethyl or acylthiomethyl groups as biolabile 2'-O-protections of RNA have been synthesized. These modified homouridylates are deprotected upon cellular esterase activation to release the parent RNA. They exhibit exceptional resistance to nuclease degradation, and the evaluation of their pairing properties shows that the 2'-acyloxymethyl groups do not prevent the duplex dsRNA formation. These biolabile 2'-modifications overcome the first hurdle to turn oligoribonucleotides into canditates for RNA interference drugs.

  DOI：

  10.1021/ol0616182

文献信息

• Assessment of new 2′-O-acetalester protecting groups for regular RNA synthesis and original 2′-modified proRNA
  作者：Anthony R. Martin、Thomas Lavergne、Jean-Jacques Vasseur、Françoise Debart

  DOI：10.1016/j.bmcl.2009.06.015

  日期：2009.8

  New base-labile acyloxymethyl groups were evaluated to protect 2′-OH functions of ribonucleotides for regular RNA synthesis in order to shorten the deprotection procedure upon ammonia. These same acetalester groups were assessed in 2′-modified proRNA as biolabile 2′-protections removable by cell enzymes to generate parent RNA. Demasking of 2′-modified pro-uridylates was studied in cell extracts.

  评估了新的对碱基不稳定的酰氧基甲基，以保护核糖核苷酸的2'-OH功能以进行常规RNA合成，从而缩短了氨气的脱保护步骤。这些相同的乙缩醛基团在2'-修饰的proRNA中评估为生物不稳定性2'-保护，可被细胞酶清除以产生亲本RNA。在细胞提取物中研究了2'-修饰的尿苷原酸酯的去掩蔽。