1-((3aR,4R,6R,6aR)-6-Hydroxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-5-(2H-quinolin-1-ylmethyl)-1H-pyrimidine-2,4-dione | 161986-79-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-((3aR,4R,6R,6aR)-6-Hydroxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-5-(2H-quinolin-1-ylmethyl)-1H-pyrimidine-2,4-dione
• CAS: 161986-79-4
• 化学式: C₂₂H₂₅N₃O₆
• 分子量: 427.457
• InChiKey: UXSWTFJGQMVTGN-SOAMZJECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.98
• 重原子数：
  31.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  106.02
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  1-((3aR,4R,6R,6aR)-6-Hydroxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-5-(2H-quinolin-1-ylmethyl)-1H-pyrimidine-2,4-dione 195.0~200.0 ℃ 、666.61 Pa 条件下， 反应 1.5h， 以12%的产率得到2',3'-O,O-isopropylidene-5-methyluridine
  参考文献：
  名称：

  Insight into the Chemical Mechanism of Thymidylate Synthase-Catalyzed Reaction Through the Evaluation of Chemical Models: The Role of C6 Sulfhydryl Addition During the Reductive Elimination Step of the Reaction1

  摘要：

  Thymidylate synthase catalyzes the last step of the de novo synthesis of thymidine-5'-monophosphate (TMP), which has long been a target for the development of effective anticancer agents. Model compounds (15, 16, 17) were used to study the effect of C6 nucleophilic addition on the reductive elimination step of the TS-catalyzed reaction. Results suggest that C6 addition facilitates the reductive elimination of the H(2)folate moiety of the ternary intermediate (3). Therefore, the reaction pathway (pathway (b)) with the participation of C6 sulfhydryl addition during the reductive elimination process is the energetically favored process. Consequently, the elimination of the cysteine sulfhydryl group from the C6 position is the last step of the reaction before the dissociation of the products from the enzyme. (C) 1994 Academic Press, Inc.

  DOI：

  10.1006/bioo.1994.1034
• 作为产物：
  描述：

  在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 1-((3aR,4R,6R,6aR)-6-Hydroxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-5-(2H-quinolin-1-ylmethyl)-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Insight into the Chemical Mechanism of Thymidylate Synthase-Catalyzed Reaction Through the Evaluation of Chemical Models: The Role of C6 Sulfhydryl Addition During the Reductive Elimination Step of the Reaction1

  摘要：

  Thymidylate synthase catalyzes the last step of the de novo synthesis of thymidine-5'-monophosphate (TMP), which has long been a target for the development of effective anticancer agents. Model compounds (15, 16, 17) were used to study the effect of C6 nucleophilic addition on the reductive elimination step of the TS-catalyzed reaction. Results suggest that C6 addition facilitates the reductive elimination of the H(2)folate moiety of the ternary intermediate (3). Therefore, the reaction pathway (pathway (b)) with the participation of C6 sulfhydryl addition during the reductive elimination process is the energetically favored process. Consequently, the elimination of the cysteine sulfhydryl group from the C6 position is the last step of the reaction before the dissociation of the products from the enzyme. (C) 1994 Academic Press, Inc.

  DOI：

  10.1006/bioo.1994.1034