3-acetyl-2-methyl-5-(2',3'-O-sulfonyl-β-D-erythrofuranosyl)pyrrole | 426818-72-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-acetyl-2-methyl-5-(2',3'-O-sulfonyl-β-D-erythrofuranosyl)pyrrole
• 英文别名: 1-[5-[(3aS,4S,6aR)-2,2-dioxo-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3,2]dioxathiol-4-yl]-2-methyl-1H-pyrrol-3-yl]ethanone
• CAS: 426818-72-6
• 化学式: C₁₁H₁₃NO₆S
• 分子量: 287.293
• InChiKey: UJNVMGJDALDYLM-OUAUKWLOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  103
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-acetyl-2-methyl-5-(2',3'-O-sulfonyl-β-D-erythrofuranosyl)pyrrole 在 四乙基氟化铵水合物 、 硫酸 作用下， 以 N,N-二甲基甲酰胺 、 四氢呋喃 、 水 为溶剂， 反应 15.0h， 以41%的产率得到3-acetyl-5-(3'-deoxy-3'-fluoro-α-L-threofuranosyl)-2-methylpyrrole
  参考文献：
  名称：

  Fluoronucleosides, Isothiocyanato C-Nucleosides, and Thioureylene Di-C-nucleosides via Cyclic Sulfates

  摘要：

  Cyclic sulfates of N- and C-nucleosides (D-ribo and D-erythro configurations, respectively) are used to prepare T-fluoro and 3'-azido D-xylo N-nucleosides and L-threo C-nucleosides. The reduction of the 3'-azido C-nucleosides (furan, imidazoline-2-thione, and pyrrole derivatives) gives T-amino C-nucleosides, which, by reaction with thiocarbonyldiimidazole, are transformed into T-isothiocyanato C-nucleosides. Reaction of the 3'-amino with the T-isothiocyanato C-nucleosides gives thioureylene di-C-nucleosides, a type of nucleotide analogue with a nonionic bridge isosteric of the phosphate group.

  DOI：

  10.1021/jo0110303
• 作为产物：
  描述：

  3-acetyl-5-(β-D-erythrofuranosyl)-2-methylpyrrole 在 sodium hydride 、 N,N-硫酰二咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以87%的产率得到3-acetyl-2-methyl-5-(2',3'-O-sulfonyl-β-D-erythrofuranosyl)pyrrole
  参考文献：
  名称：

  Fluoronucleosides, Isothiocyanato C-Nucleosides, and Thioureylene Di-C-nucleosides via Cyclic Sulfates

  摘要：

  Cyclic sulfates of N- and C-nucleosides (D-ribo and D-erythro configurations, respectively) are used to prepare T-fluoro and 3'-azido D-xylo N-nucleosides and L-threo C-nucleosides. The reduction of the 3'-azido C-nucleosides (furan, imidazoline-2-thione, and pyrrole derivatives) gives T-amino C-nucleosides, which, by reaction with thiocarbonyldiimidazole, are transformed into T-isothiocyanato C-nucleosides. Reaction of the 3'-amino with the T-isothiocyanato C-nucleosides gives thioureylene di-C-nucleosides, a type of nucleotide analogue with a nonionic bridge isosteric of the phosphate group.

  DOI：

  10.1021/jo0110303

文献信息

• Fluoronucleosides, Isothiocyanato<i> C-</i>Nucleosides, and Thioureylene Di-<i>C-</i>nucleosides via Cyclic Sulfates
  作者：José Fuentes、Manuel Angulo、M. Angeles Pradera

  DOI：10.1021/jo0110303

  日期：2002.4.1

  Cyclic sulfates of N- and C-nucleosides (D-ribo and D-erythro configurations, respectively) are used to prepare T-fluoro and 3'-azido D-xylo N-nucleosides and L-threo C-nucleosides. The reduction of the 3'-azido C-nucleosides (furan, imidazoline-2-thione, and pyrrole derivatives) gives T-amino C-nucleosides, which, by reaction with thiocarbonyldiimidazole, are transformed into T-isothiocyanato C-nucleosides. Reaction of the 3'-amino with the T-isothiocyanato C-nucleosides gives thioureylene di-C-nucleosides, a type of nucleotide analogue with a nonionic bridge isosteric of the phosphate group.