1-(3,5-di-O-t-butyldimethylsilyl-2-deoxy-D-erythro-pent-1-enofuranosyl)thymine | 175471-31-5

• 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: 1-(3,5-di-O-t-butyldimethylsilyl-2-deoxy-D-erythro-pent-1-enofuranosyl)thymine
• CAS: 175471-31-5
• 化学式: C₂₂H₄₀N₂O₅Si₂
• 分子量: 468.741
• InChiKey: PDWPQIDIUCKBGL-DLBZAZTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.45
• 重原子数：
  31.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  82.55
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1-(3,5-di-O-t-butyldimethylsilyl-2-deoxy-D-erythro-pent-1-enofuranosyl)thymine 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 三正丁基氢锡 、 四氯化锡 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 6.0h， 生成 1-(1-C-cyano-2-deoxy-3,5-di-O-t-butyldimethylsilyl-β-D-erythro-pentofuranosyl)thymine
  参考文献：
  名称：

  Synthesis and Biological Evaluation of 1′-C-Cyano-Pyrimidine Nucleosides

  摘要：

  2'-Deoxy-, 2'-bromo-, and arabine-1'-C-cyano-pyrimidine nucleosides were synthesized from O-2,2'-cyclouridine. Incorporation of cyano group at the anomeric position was achieved by treatment of 1',2'-unsaturated uridine with NBS in the presence of pivalic acid followed by TMS-cyanide and stannic chloride. Antineoplastic and antiviral activities of those compounds are also discussed.

  DOI：

  10.1080/07328319608002386
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 在 咪唑 、 potassium tert-butylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 1-(3,5-di-O-t-butyldimethylsilyl-2-deoxy-D-erythro-pent-1-enofuranosyl)thymine
  参考文献：
  名称：

  Synthesis and Biological Evaluation of 1′-C-Cyano-Pyrimidine Nucleosides

  摘要：

  2'-Deoxy-, 2'-bromo-, and arabine-1'-C-cyano-pyrimidine nucleosides were synthesized from O-2,2'-cyclouridine. Incorporation of cyano group at the anomeric position was achieved by treatment of 1',2'-unsaturated uridine with NBS in the presence of pivalic acid followed by TMS-cyanide and stannic chloride. Antineoplastic and antiviral activities of those compounds are also discussed.

  DOI：

  10.1080/07328319608002386

文献信息

• Nucleophilic Addition of Benzenethiol to 1‘,2‘-Unsaturated Nucleosides:  1‘-<i>C</i>-Phenylthio-2‘-deoxynucleosides as Anomeric Radical Precursors
  作者：Hiroki Kumamoto、Miki Murasaki、Kazuhiro Haraguchi、Aki Anamura、Hiromichi Tanaka

  DOI：10.1021/jo0201934

  日期：2002.8.1

  The addition reaction of benzenethiol to the glycal portion of 1',2'-unsaturated uridine proceeds efficiently in the presence of Et3N. The mechanism involves nucleophilic attack of thiolate at the anomeric position in the rate-determining step, wherein conjugation between the nucleobase and the glycal portion is crucial. The derivative having a methyl group either at the 2'- or 6-position did not undergo this addition reaction, due to their sterically prohibited coplanarity. The 1',2'-unsaturated derivatives of thymine and adenine can also be used as substrates for this addition reaction. It was also shown that the resulting 1'-C-phenylthio-2'-deoxynucleosides serve as precursors for radical-mediated C-C bond formation at the anomeric position.