4,5-dimethyl-2-nitro-N-(2',3',5'-tri-O-acetyl-α-D-ribofuranosyl)benzenamine | 312715-32-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4,5-dimethyl-2-nitro-N-(2',3',5'-tri-O-acetyl-α-D-ribofuranosyl)benzenamine
• 英文别名: [(2R,3R,4R,5S)-3,4-diacetyloxy-5-(4,5-dimethyl-2-nitroanilino)oxolan-2-yl]methyl acetate
• CAS: 312715-32-5
• 化学式: C₁₉H₂₄N₂O₉
• 分子量: 424.408
• InChiKey: JQFXRKXLLYRHLI-MKXGPGLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.77
• 重原子数：
  30.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  143.3
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  4,5-dimethyl-2-nitro-N-(2',3',5'-tri-O-acetyl-α-D-ribofuranosyl)benzenamine 在 platinum(IV) oxide 氢气 、 硼酸 、 溶剂黄146 、 三乙胺 作用下， 以 乙酸乙酯 为溶剂， 20.0 ℃ 、200.0 kPa 条件下， 反应 2.0h， 生成 7,8-dimethyl-10-(2',3',5'-tri-O-acetyl-α-D-ribofuranosyl)benzo[g]pteridine-2,4(3H,10H)-dione
  参考文献：
  名称：

  Synthesis and Properties of Flavin Ribofuranosides and Flavin Ribopyranosides

  摘要：

  Ribose-containing coenzymes like flavin mononucleotide (FMN) can be considered to be fossils of a prebiotic RNA world in which RNA encoded genetic information and catalyzed chemical reactions. To investigate the catalytic and base-pairing properties of FMN-containing oligonucleotides, the two cyclic flavin beta-D-ribosides 3 and 4 derived from riboflavin 2 were synthesized (Schemes 1 and 2). These are both constitutionally strongly related to the nucleobase uridine and should be able to participate as catalytically competent and informational nucleobases in DNA RNA, and p-RNA. Ribofuranaside 3 was too unstable to be isolated, but ribopyranoside 4 had the required stability, beta-D-configuration, and anti-conformation of the glycosidic bond.

  DOI：

  10.1002/1522-2675(20000906)83:9<2452::aid-hlca2452>3.0.co;2-6
• 作为产物：
  描述：

  benzyl-β-D-ribofuranoside 在 氢气 、 氯化铵 作用下， 以 吡啶 、 甲醇 、 乙醇 为溶剂， 反应 2.5h， 生成 4,5-dimethyl-2-nitro-N-(2',3',5'-tri-O-acetyl-α-D-ribofuranosyl)benzenamine
  参考文献：
  名称：

  Synthesis and Properties of Flavin Ribofuranosides and Flavin Ribopyranosides

  摘要：

  Ribose-containing coenzymes like flavin mononucleotide (FMN) can be considered to be fossils of a prebiotic RNA world in which RNA encoded genetic information and catalyzed chemical reactions. To investigate the catalytic and base-pairing properties of FMN-containing oligonucleotides, the two cyclic flavin beta-D-ribosides 3 and 4 derived from riboflavin 2 were synthesized (Schemes 1 and 2). These are both constitutionally strongly related to the nucleobase uridine and should be able to participate as catalytically competent and informational nucleobases in DNA RNA, and p-RNA. Ribofuranaside 3 was too unstable to be isolated, but ribopyranoside 4 had the required stability, beta-D-configuration, and anti-conformation of the glycosidic bond.

  DOI：

  10.1002/1522-2675(20000906)83:9<2452::aid-hlca2452>3.0.co;2-6