7,8-dimethyl-10-(2',3',5'-tri-O-acetyl-β-D-ribopyranosyl)benzo[g]pteridine-2,4(3H,10H)-dione | 312715-30-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 7,8-dimethyl-10-(2',3',5'-tri-O-acetyl-β-D-ribopyranosyl)benzo[g]pteridine-2,4(3H,10H)-dione
• 英文别名: [(3R,4R,5R,6R)-4,5-diacetyloxy-6-(7,8-dimethyl-2,4-dioxobenzo[g]pteridin-10-yl)oxan-3-yl] acetate
• CAS: 312715-30-3
• 化学式: C₂₃H₂₄N₄O₉
• 分子量: 500.465
• InChiKey: VOTKWDKQQOUAQF-WGQQHEPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  36
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  162
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  7,8-dimethyl-10-(2',3',5'-tri-O-acetyl-β-D-ribopyranosyl)benzo[g]pteridine-2,4(3H,10H)-dione 在 氨 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以48%的产率得到7,8-dimethyl-10-(β-D-ribopyranosyl)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：

  4,5-dimethyl-2-nitro-N-(2',3',5'-tri-O-acetyl-α-D-ribopyranosyl)benzenamine 在 platinum(IV) oxide 氢气 、 硼酸 、 三乙胺 作用下， 以 溶剂黄146 、 乙酸乙酯 为溶剂， 反应 3.0h， 生成 7,8-dimethyl-10-(2',3',5'-tri-O-acetyl-β-D-ribopyranosyl)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