6-amino-3-{3'-[(1,1-dimethylethyl)diphenylsilyloxy]-β-D-glycero-pentofuran-3'-ulos-1'-yl}-5-nitro-1H-pyridin-2-one | 642460-97-7

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 6-amino-3-{3'-[(1,1-dimethylethyl)diphenylsilyloxy]-β-D-glycero-pentofuran-3'-ulos-1'-yl}-5-nitro-1H-pyridin-2-one
• 英文别名: 6-amino-3-[(2R,5R)-4-[tert-butyl(diphenyl)silyl]oxy-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-5-nitro-1H-pyridin-2-one
• CAS: 642460-97-7
• 化学式: C₂₆H₂₉N₃O₆Si
• 分子量: 507.618
• InChiKey: GALMSOVNBYRREN-FYYLOGMGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.76
• 重原子数：
  36
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  140
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  6-amino-3-{3'-[(1,1-dimethylethyl)diphenylsilyloxy]-β-D-glycero-pentofuran-3'-ulos-1'-yl}-5-nitro-1H-pyridin-2-one 在 四丁基氟化铵 、 三乙酰氧基硼氢化钠 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 1.08h， 生成 6-amino-5-nitro-3-(1'-β-D-2'-deoxyribofuranosyl)-2(1H)-pyridone
  参考文献：
  名称：

  Expanding the Genetic Alphabet:  Non-Epimerizing Nucleoside with the pyDDA Hydrogen-Bonding Pattern

  摘要：

  6-Amino-3-(2'-deoxy-beta-D-ribofuranosyl)-5-nitro-1H-pyridin-2-one (4), a C-glycoside exhibiting the nonstandard pgammaDDA hydrogen-bonding pattern, was synthesized via Heck coupling. The nitro group greatly enhances the stability of the nucleoside toward acid-catalyzed epimerization without leading to significant deprotonation of the heterocycle at physiological pH. These results make nucleoside 4 a promising candidate for an expanded genetic alphabet.

  DOI：

  10.1021/jo034900k
• 作为产物：
  描述：

  2-氨基-3-硝基吡啶 在 palladium diacetate 、 N-碘代丁二酰亚胺 、 potassium acetate 、 乙酸酐 、 三乙胺 、 间氯过氧苯甲酸 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 332.25h， 生成 6-amino-3-{3'-[(1,1-dimethylethyl)diphenylsilyloxy]-β-D-glycero-pentofuran-3'-ulos-1'-yl}-5-nitro-1H-pyridin-2-one
  参考文献：
  名称：

  Expanding the Genetic Alphabet:  Non-Epimerizing Nucleoside with the pyDDA Hydrogen-Bonding Pattern

  摘要：

  6-Amino-3-(2'-deoxy-beta-D-ribofuranosyl)-5-nitro-1H-pyridin-2-one (4), a C-glycoside exhibiting the nonstandard pgammaDDA hydrogen-bonding pattern, was synthesized via Heck coupling. The nitro group greatly enhances the stability of the nucleoside toward acid-catalyzed epimerization without leading to significant deprotonation of the heterocycle at physiological pH. These results make nucleoside 4 a promising candidate for an expanded genetic alphabet.

  DOI：

  10.1021/jo034900k

文献信息

• Expanding the Genetic Alphabet:  Non-Epimerizing Nucleoside with the <i>py</i>DDA Hydrogen-Bonding Pattern
  作者：Daniel Hutter、Steven A. Benner

  DOI：10.1021/jo034900k

  日期：2003.12.1

  6-Amino-3-(2'-deoxy-beta-D-ribofuranosyl)-5-nitro-1H-pyridin-2-one (4), a C-glycoside exhibiting the nonstandard pgammaDDA hydrogen-bonding pattern, was synthesized via Heck coupling. The nitro group greatly enhances the stability of the nucleoside toward acid-catalyzed epimerization without leading to significant deprotonation of the heterocycle at physiological pH. These results make nucleoside 4 a promising candidate for an expanded genetic alphabet.