1-(3,5-di-O-p-toluoyl-2-deoxy-β-D-erythro-pentofuranosyl)quinozaline-2,4(3H)-dione | 15135-28-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 1-(3,5-di-O-p-toluoyl-2-deoxy-β-D-erythro-pentofuranosyl)quinozaline-2,4(3H)-dione
• 英文别名: 1-[O³,O⁵-bis-(4-methyl-benzoyl)-β-D-erythro-2-deoxy-pentofuranosyl]-1H-quinazoline-2,4-dione；1-(3',5'-Di-O-p-toluoyl-2'-desoxy-β-D-ribofuranosyl)-1,2,3,4-tetrahydro-chinazolin-2,4-dion；[(2R,3S,5R)-5-(2,4-dioxoquinazolin-1-yl)-3-(4-methylbenzoyl)oxyoxolan-2-yl]methyl 4-methylbenzoate
• CAS: 15135-28-1
• 化学式: C₂₉H₂₆N₂O₇
• 分子量: 514.535
• InChiKey: PPSJXEDDXCJNSC-ISJGIBHGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  38
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2,4-喹唑啉二酮 在 乙酰胺 、 硫酸氢铵 作用下， 以 氯仿 为溶剂， 反应 60.0h， 生成 1-(3,5-di-O-p-toluoyl-2-deoxy-β-D-erythro-pentofuranosyl)quinozaline-2,4(3H)-dione
  参考文献：
  名称：

  An Improved Synthesis of 1-(2-Deoxy-β-D-erythro-pentofuranosyl)quinazoline-2,4(3H)-dione and Its Incorporation Into G-Rich Triple Helix Forming Oligonucleotides

  摘要：

  A convenient synthesis of 1-(2-deoxy-beta-D-erythro-pentofuranosyl)quinazoline-2,4(3H)-dione (6) has been accomplished. The structural conformation of (6) was derived by 2D NMR, COSY and NOESY experiments. Nucleoside (6) was incorporated into G-rich tripler forming oligonucleotides (TFOs) by solid-support, phosphoramidite method. The tripler forming capabilities of modified TFOs (S2, S3 and S4) has been evaluated in antiparallel motif with a target duplex (duplex-31) 5'd(GTCACTGGCCCTTCCTCCTTCCCGGTCTCAG)3'-5'd(CAGTGACCGGGAAGGAGGAAGGGCCAGAGTC)3' (D1) at pH 7.6. The parallel tripler formation of a shorter TFO (S6) containing Q has also been studied with a target duplex-11 (D2) at PH 5.0.

  DOI：

  10.1080/15257779508014652

文献信息

• An Improved Synthesis of 1-(2-Deoxy-β-D-erythro-pentofuranosyl)quinazoline-2,4(3<i>H</i>)-dione and Its Incorporation Into G-Rich Triple Helix Forming Oligonucleotides
  作者：Birendra K. Bhattacharya、Mohan V. Chari、Ross H. Durland、Ganapathi R. Revankar

  DOI：10.1080/15257779508014652

  日期：1995.2

  A convenient synthesis of 1-(2-deoxy-beta-D-erythro-pentofuranosyl)quinazoline-2,4(3H)-dione (6) has been accomplished. The structural conformation of (6) was derived by 2D NMR, COSY and NOESY experiments. Nucleoside (6) was incorporated into G-rich tripler forming oligonucleotides (TFOs) by solid-support, phosphoramidite method. The tripler forming capabilities of modified TFOs (S2, S3 and S4) has been evaluated in antiparallel motif with a target duplex (duplex-31) 5'd(GTCACTGGCCCTTCCTCCTTCCCGGTCTCAG)3'-5'd(CAGTGACCGGGAAGGAGGAAGGGCCAGAGTC)3' (D1) at pH 7.6. The parallel tripler formation of a shorter TFO (S6) containing Q has also been studied with a target duplex-11 (D2) at PH 5.0.