N1-methyl-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2'-O-<(imidazol-1-yl)thiocarbonyl>-ψ-uridine | 80545-47-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: N1-methyl-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2'-O-<(imidazol-1-yl)thiocarbonyl>-ψ-uridine
• 英文别名: 1-methyl-3',5'-O-(tetraisopropyldisiloxanyl)-2'-O-<(imidazol-1-yl)thiocarbonyl>pseudouridine；1-methyl-3',5'-O-(tetraisopropyldisiloxanyl)-2'-O-[(imidazol-1-yl)thiocarbonyl]pseudouridine；O-[(6aR,8S,9S,9aR)-8-(1-methyl-2,4-dioxopyrimidin-5-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] imidazole-1-carbothioate
• CAS: 80545-47-7
• 化学式: C₂₆H₄₂N₄O₇SSi₂
• 分子量: 610.879
• InChiKey: CJUCZEDBEIUANV-ACESQOTJSA-N

物化性质

• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.88
• 重原子数：
  40
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  146
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N1-methyl-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2'-O-<(imidazol-1-yl)thiocarbonyl>-ψ-uridine 在 偶氮二异丁腈 、 四丁基氟化铵 、 三正丁基氢锡 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 吡啶 、 二氯甲烷 、 甲苯 为溶剂， 反应 6.75h， 生成 N1-methyl-5'->-3'-<2-cyanoethyl bis(1-methylethyl)>phosphoramidite
  参考文献：
  名称：

  A Practical Synthesis ofN1-Methyl-2′-deoxy-ψ-uridine (ψ-Thymidine) and Its Incorporation into G-Rich Triple Helix Forming Oligonucleotides

  摘要：

  A convenient synthesis of N1-methyl-2'-deoxy-psi-uridine (psi-thymidine, psi T, 7a) has been accomplished in good yield. The structural conformation of 7a was derived by 2D NMR and 1D NOE experiments. The nucleoside 7a has been incorporated into G-rich tripler forming oligonucleotides (TFOs) by solid-support, phosphoramidite method. The tripler forming capabilities of the modified TFOs (S4, S5 and S6) containing psi T has been evaluated in antiparallel motif with a target duplex (duplex-31) 5'd(CTGAGACCGGGAAGGAGGAAGGGCCAGTGAC)3'-5d(GACTCTGGCCCTTCCTCCTTCCCGGTCACTG)3' (D1) at pH 7.6. The tripler formation of modified homopyrimidine-oligomers (S1, S2 and S3) has also been studied in parallel motif with a duplex-10 (A(10):T-10) at pH 7.0.

  DOI：

  10.1080/15257779508010690
• 作为产物：
  描述：

  假尿苷 在 苯磺酰胺 、 4-二甲氨基吡啶 、 氨 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 37.5h， 生成 N1-methyl-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2'-O-<(imidazol-1-yl)thiocarbonyl>-ψ-uridine
  参考文献：
  名称：

  A Practical Synthesis ofN1-Methyl-2′-deoxy-ψ-uridine (ψ-Thymidine) and Its Incorporation into G-Rich Triple Helix Forming Oligonucleotides

  摘要：

  A convenient synthesis of N1-methyl-2'-deoxy-psi-uridine (psi-thymidine, psi T, 7a) has been accomplished in good yield. The structural conformation of 7a was derived by 2D NMR and 1D NOE experiments. The nucleoside 7a has been incorporated into G-rich tripler forming oligonucleotides (TFOs) by solid-support, phosphoramidite method. The tripler forming capabilities of the modified TFOs (S4, S5 and S6) containing psi T has been evaluated in antiparallel motif with a target duplex (duplex-31) 5'd(CTGAGACCGGGAAGGAGGAAGGGCCAGTGAC)3'-5d(GACTCTGGCCCTTCCTCCTTCCCGGTCACTG)3' (D1) at pH 7.6. The tripler formation of modified homopyrimidine-oligomers (S1, S2 and S3) has also been studied in parallel motif with a duplex-10 (A(10):T-10) at pH 7.0.

  DOI：

  10.1080/15257779508010690

文献信息

• Nucleosides. 121. Improved and general synthesis of 2'-deoxy-C-nucleosides. Synthesis of 5-(2-deoxy-.beta.-D-erythro-pentofuranosyl)uracil, -1-methyluracil, -1,3-dimethyluracil, and -isocytosine
  作者：Krzysztof Pankiewicz、Akira Matsuda、Kyoichi A. Watanabe

  DOI：10.1021/jo00342a022

  日期：1982.1
• A Practical Synthesis of<i>N</i>1-Methyl-2′-deoxy-ψ-uridine (ψ-Thymidine) and Its Incorporation into G-Rich Triple Helix Forming Oligonucleotides
  作者：Birendra K. Bhattacharya、Rodrigo V. Devivar、Ganapathi R. Revankar

  DOI：10.1080/15257779508010690

  日期：1995.8

  A convenient synthesis of N1-methyl-2'-deoxy-psi-uridine (psi-thymidine, psi T, 7a) has been accomplished in good yield. The structural conformation of 7a was derived by 2D NMR and 1D NOE experiments. The nucleoside 7a has been incorporated into G-rich tripler forming oligonucleotides (TFOs) by solid-support, phosphoramidite method. The tripler forming capabilities of the modified TFOs (S4, S5 and S6) containing psi T has been evaluated in antiparallel motif with a target duplex (duplex-31) 5'd(CTGAGACCGGGAAGGAGGAAGGGCCAGTGAC)3'-5d(GACTCTGGCCCTTCCTCCTTCCCGGTCACTG)3' (D1) at pH 7.6. The tripler formation of modified homopyrimidine-oligomers (S1, S2 and S3) has also been studied in parallel motif with a duplex-10 (A(10):T-10) at pH 7.0.