5'-thioacetyl-2',3'-O-isopropylidenethymidine | 161986-84-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 5'-thioacetyl-2',3'-O-isopropylidenethymidine
• 英文别名: S-[[(3aR,4R,6S,6aS)-2,2-dimethyl-4-(5-methyl-2,4-dioxopyrimidin-1-yl)-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methyl] ethanethioate
• CAS: 161986-84-1
• 化学式: C₁₅H₂₀N₂O₆S
• 分子量: 356.4
• InChiKey: KUPJDJDVXGVXAR-PRULPYPASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  120
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5'-thioacetyl-2',3'-O-isopropylidenethymidine 在 potassium carbonate 、 苯甲醛 作用下， 以 甲醇 为溶剂， 生成 5'-thiol-2',3'-O-isopropylidenethymidine disulfide
  参考文献：
  名称：

  嘧啶/羟醛串联反应条件下嘧啶核碱基C5C6键反应性的研究

  摘要：

  嘧啶核苷可以经历由硫醇盐引发的迈克尔/羟醛串联反应。在分子内，5'-脱氧-2'，3'-异亚丙基-5'-硫尿苷在反式迈克尔加成后提供让人想起的Baylis-Hillman加合物，而其胸腺嘧啶对应的则无反应性。在分子间的情况下，仅当C5 C6双键被激活时，才会发生共轭加成-羟醛反应。

  DOI：

  10.1002/jhet.5570430442
• 作为产物：
  描述：

  2',3'-O,O-isopropylidene-5-methyluridine 在 吡啶 作用下， 以 丙酮 为溶剂， 反应 65.0h， 生成 5'-thioacetyl-2',3'-O-isopropylidenethymidine
  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

文献信息

• Study of the pyrimidine nucleobase C5C6 bond reactivity under thio-michael/aldol tandem reaction conditions
  作者：Edna Vázquez Velez、Céline Desnous、Pascale Clivio

  DOI：10.1002/jhet.5570430442

  日期：2006.7

  Pyrimidine nucleobases can undergo a Michael/aldol tandem reaction triggered by a thiolate. In an intramolecular context, 5′-deoxy-2′,3′-isopropylidene-5′-thiouridine affords the reminiscent Baylis-Hillman adduct after retro-Michael addition whereas its thymine counterpart is unreactive. In an intermolecular context, the conjugate addition-aldol reaction occurs only if the C5C6 double bond is activated

  嘧啶核苷可以经历由硫醇盐引发的迈克尔/羟醛串联反应。在分子内，5'-脱氧-2'，3'-异亚丙基-5'-硫尿苷在反式迈克尔加成后提供让人想起的Baylis-Hillman加合物，而其胸腺嘧啶对应的则无反应性。在分子间的情况下，仅当C5 C6双键被激活时，才会发生共轭加成-羟醛反应。
• 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
  作者：B.H. Wang、J.R. Kagel、M.P. Mertes、K. Bowmanjames

  DOI：10.1006/bioo.1994.1034

  日期：1994.12

  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.