N2-(Dimethylamino)methylene-2',3',5'-tri-O-TBDMS-β-D-ribofuranosyl-guanosine | 145744-07-6

• 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: N2-(Dimethylamino)methylene-2',3',5'-tri-O-TBDMS-β-D-ribofuranosyl-guanosine
• 英文别名: N'-[9-[(2R,3R,4R,5R)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-5-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-2-yl]-6-oxo-1H-purin-2-yl]-N,N-dimethylmethanimidamide
• CAS: 145744-07-6
• 化学式: C₃₁H₆₀N₆O₅Si₃
• 分子量: 681.111
• InChiKey: NLHNMJDFHRSCEV-VBHAUSMQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.04
• 重原子数：
  45
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  112
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N2-(Dimethylamino)methylene-2',3',5'-tri-O-TBDMS-β-D-ribofuranosyl-guanosine 在 乙醇 、 乙二胺 作用下， 生成 2',3',5'-tri-O-(tert-butyldimethylsilyl)guanosine
  参考文献：
  名称：

  Tricyclic “oxadiazaphosphorine oxide” guanosines: A new strategy to the protection of guanine bases during RNA synthesis

  摘要：

  A novel strategy for simultaneously protecting the lactam and N2-amino functions of guanine nucleosides is reported. N2-benzoylated guanosines were readily converted into tricyclic "oxadiazaphosphorine oxide" guanosines upon reaction with N,N-diisopropylphosphoramidous dichloride followed by oxidation with t-butyl hydroperoxide. The tricyclic guanine derivative is reconverted readily to the natural guanine aglycone upon treatment with ethylenediamine/ethanol (1:4, 1 min, r.t.).

  DOI：

  10.1016/s0040-4039(00)61764-1

文献信息

• Ceric Ammonium Nitrate on Silica Gel for Efficient and Selective Removal of Trityl and Silyl Groups
  作者：Jih Ru Hwu、Moti L. Jain、Fu-Yuan Tsai、Shwu-Chen Tsay、Arumugham Balakumar、Gholam H. Hakimelahi

  DOI：10.1021/jo000024o

  日期：2000.8.1

  triisopropylsilyl group from a primary hydroxyl functionality in di- or trisilyl ethers of ribonucleosides. A comparative study of deprotection reactions by utilization of CAN alone or CAN-SiO2 indicates a remarkable increase in the rate of the reactions involving a solid support. The mechanism of electron-transfer processes is proposed for the use of CAN-SiO2 in the removal of these protective groups from organic

  发现硅胶负载的硝酸铈铵（CAN-SiO2）在温和条件下可从受保护的核苷和核苷酸中快速选择性地裂解三苯甲基（Tr），单甲氧基三苯甲基（MMTr）和二甲氧基三苯甲基（DMTr）基团。脱保护的效率取决于所得碳阳离子物质的稳定性：DMTr +> MMTr +> Tr +。使用催化量的这种固体负载的试剂还可以有效地和选择性地从核糖核苷的二或三甲硅烷基醚中的伯羟基官能团中除去叔丁基二甲基甲硅烷基或三异丙基甲硅烷基。通过单独使用CAN或CAN-SiO2进行脱保护反应的比较研究表明，涉及固相支持物的反应速率显着提高。
• Tricyclic “oxadiazaphosphorine oxide” guanosines: A new strategy to the protection of guanine bases during RNA synthesis
  作者：Masad J. Damha、Yunkui Guo、Steve V. Zabarylo、Kanjana Ganeshan、Paul A. Giannaris

  DOI：10.1016/s0040-4039(00)61764-1

  日期：1992.11

  A novel strategy for simultaneously protecting the lactam and N2-amino functions of guanine nucleosides is reported. N2-benzoylated guanosines were readily converted into tricyclic "oxadiazaphosphorine oxide" guanosines upon reaction with N,N-diisopropylphosphoramidous dichloride followed by oxidation with t-butyl hydroperoxide. The tricyclic guanine derivative is reconverted readily to the natural guanine aglycone upon treatment with ethylenediamine/ethanol (1:4, 1 min, r.t.).