N-(2',3'-O-isopropylidene-α-D-ribofuranosyl)-4,5-dimethyl-2-nitrobenzenamine | 312715-34-7

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: N-(2',3'-O-isopropylidene-α-D-ribofuranosyl)-4,5-dimethyl-2-nitrobenzenamine
• CAS: 312715-34-7
• 化学式: C₁₆H₂₂N₂O₆
• 分子量: 338.36
• InChiKey: IVOOIMDQGOFGFX-TUVASFSCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.86
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  103.09
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  N-(2',3'-O-isopropylidene-α-D-ribofuranosyl)-4,5-dimethyl-2-nitrobenzenamine 在 PO₂ 氢气 、 三乙胺 作用下， 以 吡啶 、 乙酸乙酯 为溶剂， 50.0 ℃ 、200.0 kPa 条件下， 反应 9.0h， 生成 Acetic acid (3aR,4R,6S,6aR)-6-(2-amino-4,5-dimethyl-phenylamino)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester
  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：

  2,3-异亚丙氧基-D-呋喃核糖苷 、 4，5-二甲-2-硝基苯胺 在 氯化铵 作用下， 以 乙醇 为溶剂， 反应 2.5h， 以66%的产率得到N-(2',3'-O-isopropylidene-α-D-ribofuranosyl)-4,5-dimethyl-2-nitrobenzenamine
  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