Acetic acid (3aR,4R,6S,6aR)-6-(2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester | 77405-85-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid (3aR,4R,6S,6aR)-6-(2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester
• CAS: 77405-85-7
• 化学式: C₁₄H₁₇NO₇
• 分子量: 311.291
• InChiKey: ZDCNCMNFLIYTOA-STRQVWJDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.28
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  91.37
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (3aR,4R,6S,6aR)-6-(2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 0.67h， 以100%的产率得到Acetic acid (3aR,4R,6S,6aR)-6-(2,5-dioxo-pyrrolidin-1-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester
  参考文献：
  名称：

  Showdomycin analogs: synthesis and antitumor evaluation

  摘要：

  The synthesis of N-beta-D-ribofuranosyl derivatives of maleimide, 3-methylmaleimide, and 3-chloromaleimide was accomplished in three steps from ribosylamine. The synthetic ribosides can be considered N-nucleoside analogues of showdomycin, which is an antitumor antibiotic of the C-nucleoside type. Although the three analogues were cytotoxic to cultured L1210 cells, no in vivo antitumor activity was found with the murine P388 leukemia test system. Drug transport studies were done in an attempt to trace the biological fate of the analogues.

  DOI：

  10.1021/jm00137a008
• 作为产物：
  描述：

  马来酸酐 、 2,3-O-Isopropylidene-D-ribofuranosylamine 、 乙酸酐 在 sodium acetate 作用下， 生成 Acetic acid (3aR,4R,6S,6aR)-6-(2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester 、 1-<5-O-acetyl-2,3-O-(1-methylethylidene)-β-D-ribofuranosyl>-1H-pyrrole-2,5-dione
  参考文献：
  名称：

  Showdomycin analogs: synthesis and antitumor evaluation

  摘要：

  The synthesis of N-beta-D-ribofuranosyl derivatives of maleimide, 3-methylmaleimide, and 3-chloromaleimide was accomplished in three steps from ribosylamine. The synthetic ribosides can be considered N-nucleoside analogues of showdomycin, which is an antitumor antibiotic of the C-nucleoside type. Although the three analogues were cytotoxic to cultured L1210 cells, no in vivo antitumor activity was found with the murine P388 leukemia test system. Drug transport studies were done in an attempt to trace the biological fate of the analogues.

  DOI：

  10.1021/jm00137a008