2'-O-azidomethyl-3',5'-O-(1,1,3,3-tetraisopropyldisilox-1,3-diyl)uridine | 329032-87-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2'-O-azidomethyl-3',5'-O-(1,1,3,3-tetraisopropyldisilox-1,3-diyl)uridine
• 英文别名: 1-((6aR,8R,9R,9aR)-3-azidomethoxy-5,5,7,7-tetraisopropyltetrahydro-1,4,6,8-tetraoxa-5,7-disilacyclopentacycloocten-2-yl)-1H-pyrimidine-2,4-dione；1-[(6aR,8R,9R,9aR)-9-(azidomethoxy)-2,2,4,4-tetra(propan-2-yl)-6a,8,9,9a-tetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl]pyrimidine-2,4-dione
• CAS: 329032-87-3
• 化学式: C₂₂H₃₉N₅O₇Si₂
• 分子量: 541.752
• InChiKey: PDMBBDBPCJVMCD-CWJKEVGVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.04
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2'-O-azidomethyl-3',5'-O-(1,1,3,3-tetraisopropyldisilox-1,3-diyl)uridine 在 吡啶 、 四丁基氟化铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 5'-O-(4,4'-dimethoxytrityl)-2'-O-azidomethyluridine
  参考文献：
  名称：

  2′-O-[(4-CF₃-triazol-1-yl)methyl] Uridine – A Sensitive ¹⁹F NMR Sensor for the Detection of RNA Secondary Structures

  摘要：

  A sensitive uridine-derived sensor (viz., 2'-O-[(4-CF3-triazol-1-yOmethyl]uridine, 1) for F-19 NMR spectroscopic monitoring of RNA secondary structures is described. The applicability of 1 is demonstrated by monitoring the thermal denaturation of the following double and triple helical RNA models: (1) a miR 215 hairpin, (2) a poly U-A*U triple helix RNA (bearing two C-G*CH+ interrupts), and (3) a polyadenylated nuclear-nuclear retention element complex. In these RNA models, the F-19 NMR shift of the 2'-O-(CF3-triazolylmethyl) group shows high sensitivity to secondary structural arrangements. Moreover, 1 favors the desired N-conformation, and its effect on both RNA duplex and triplex stabilities is marginal.

  DOI：

  10.1021/acs.joc.5b00973
• 作为产物：
  描述：

  3',5'-O-(1,1,3,3-四异丙基-1,3-二硅氧烷)尿苷 在 sodium azide 、 溴 、 乙酸酐 、 溶剂黄146 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 73.0h， 生成 2'-O-azidomethyl-3',5'-O-(1,1,3,3-tetraisopropyldisilox-1,3-diyl)uridine
  参考文献：
  名称：

  Tracking of nascent deoxynucleic acids enable by incorporation of uridine variant with 2 prime azidomethyl tag and click chemistry

  摘要：

  DOI：

  10.1016/j.tetlet.2022.153678

文献信息

• S,<i>X</i>-Acetals in Nucleoside Chemistry. III¹. Synthesis of 2′-and 3′-O-Azidomethyl Derivatives of Ribonucleosides
  作者：S. G. Zavgorodny、A. E. Pechenov、V. I. Shvets、A. I. Miroshnikov

  DOI：10.1080/15257770008045472

  日期：2000.10

  2'- and 3'-O-azidomethyl derivatives of ribonucleosides were obtained by splitting the corresponding methylthiomethyl derivatives of ribonucleosides with bromine or SO2Cl2 followed by lithium azide treatment.

  核糖核苷的2'-和3'-O-叠氮甲基衍生物是通过用溴或SO2Cl2拆分核糖核苷的相应甲硫基甲基衍生物，然后进行叠氮化锂处理而获得的。
• 2′-<i>O</i>-[(4-CF₃-triazol-1-yl)methyl] Uridine – A Sensitive ¹⁹F NMR Sensor for the Detection of RNA Secondary Structures
  作者：Lotta Granqvist、Pasi Virta

  DOI：10.1021/acs.joc.5b00973

  日期：2015.8.21

  A sensitive uridine-derived sensor (viz., 2'-O-[(4-CF3-triazol-1-yOmethyl]uridine, 1) for F-19 NMR spectroscopic monitoring of RNA secondary structures is described. The applicability of 1 is demonstrated by monitoring the thermal denaturation of the following double and triple helical RNA models: (1) a miR 215 hairpin, (2) a poly U-A*U triple helix RNA (bearing two C-G*CH+ interrupts), and (3) a polyadenylated nuclear-nuclear retention element complex. In these RNA models, the F-19 NMR shift of the 2'-O-(CF3-triazolylmethyl) group shows high sensitivity to secondary structural arrangements. Moreover, 1 favors the desired N-conformation, and its effect on both RNA duplex and triplex stabilities is marginal.
• Tracking of nascent deoxynucleic acids enable by incorporation of uridine variant with 2 prime azidomethyl tag and click chemistry
  作者：Hongling Zhou、Yuanyuan Li、Sheng Wang、Li Wang、Rui Wang

  DOI：10.1016/j.tetlet.2022.153678

  日期：2022.3