1-β-D-[8-(2,4-dimethoxy-6-methylquinazoline)]-2'-deoxyribofuranose | 667916-44-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-β-D-[8-(2,4-dimethoxy-6-methylquinazoline)]-2'-deoxyribofuranose
• 英文别名: (2R,3S,5R)-5-(2,4-dimethoxy-6-methylquinazolin-8-yl)-2-(hydroxymethyl)oxolan-3-ol
• CAS: 667916-44-1
• 化学式: C₁₆H₂₀N₂O₅
• 分子量: 320.345
• InChiKey: FQCJJLHMDRJCFU-YNEHKIRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  93.9
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-β-D-[8-(2,4-dimethoxy-6-methylquinazoline)]-2'-deoxyribofuranose 在 吡啶 、 溶剂黄146 、 N,N-二异丙基乙胺 、 sodium iodide 作用下， 反应 6.75h， 生成 1'-β-D-[8-(6-methylquinazoline-2,4-dione)]-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyribofuranose
  参考文献：
  名称：

  Toward a New Genetic System with Expanded Dimensions:  Size-Expanded Analogues of Deoxyadenosine and Thymidine

  摘要：

  We describe the design, preparation, and properties of two key building blocks of a size-expanded genetic system. Nucleoside analogues of the natural nucleosides dA and dT are reported in which the fusion of a benzo ring increases their size by ca. 2.4 Angstrom. The expanded dA analogue (dxA), having a tricyclic base, was first reported by Leonard nearly three decades ago. We describe a shortened and more efficient approach to this compound. The expanded dT analogue (dxT), a methylquinazolinedione C-glycoside, was previously unknown; we describe its preparation in eight steps from 5-methylanthranilic acid. The key glycoside bond formation employed Pd-mediated coupling of an aryl iodide precursor with a dihydrofuran derivative of deoxyribose. Both nucleosides are shown to be efficient fluorophores, emitting light in the blue-violet range. The base-protected phosphoramidite derivatives were prepared, and short oligonucleotides containing them were characterized. The two size-expanded nuclecisides are key components of a new four-base genetic system designed to form helical paired structures having a diameter greater than that of natural DNA. Elements of the design of this expanded genetic molecule, termed xDNA, are discussed, including the possibility of up to eight base pairs of information storage capability.

  DOI：

  10.1021/ja038384r
• 作为产物：
  描述：

  2,4-dimethoxy-8-(β-D-glyceropentofuran-3'-ulos-1'-yl)-6-methylquinazoline 在 三乙酰氧基硼氢化钠 、 溶剂黄146 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以93%的产率得到1-β-D-[8-(2,4-dimethoxy-6-methylquinazoline)]-2'-deoxyribofuranose
  参考文献：
  名称：

  Toward a New Genetic System with Expanded Dimensions:  Size-Expanded Analogues of Deoxyadenosine and Thymidine

  摘要：

  We describe the design, preparation, and properties of two key building blocks of a size-expanded genetic system. Nucleoside analogues of the natural nucleosides dA and dT are reported in which the fusion of a benzo ring increases their size by ca. 2.4 Angstrom. The expanded dA analogue (dxA), having a tricyclic base, was first reported by Leonard nearly three decades ago. We describe a shortened and more efficient approach to this compound. The expanded dT analogue (dxT), a methylquinazolinedione C-glycoside, was previously unknown; we describe its preparation in eight steps from 5-methylanthranilic acid. The key glycoside bond formation employed Pd-mediated coupling of an aryl iodide precursor with a dihydrofuran derivative of deoxyribose. Both nucleosides are shown to be efficient fluorophores, emitting light in the blue-violet range. The base-protected phosphoramidite derivatives were prepared, and short oligonucleotides containing them were characterized. The two size-expanded nuclecisides are key components of a new four-base genetic system designed to form helical paired structures having a diameter greater than that of natural DNA. Elements of the design of this expanded genetic molecule, termed xDNA, are discussed, including the possibility of up to eight base pairs of information storage capability.

  DOI：

  10.1021/ja038384r