5-(1-Thiapentyl)-2'-deoxyuridine | 21740-34-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 5-(1-Thiapentyl)-2'-deoxyuridine
• 英文别名: 5-butylsulfanyl-2'-deoxy-uridine；5-butylsulfanyl-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
• CAS: 21740-34-1
• 化学式: C₁₃H₂₀N₂O₅S
• 分子量: 316.378
• InChiKey: JLBJFBWZJWTFHA-IQJOONFLSA-N

物化性质

• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  124
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  二丁基二硫 、 5-(chloromercuri)-2'-deoxyuridine 在 lithium tetrachloropalladate 作用下， 以 甲醇 为溶剂， 以73%的产率得到5-(1-Thiapentyl)-2'-deoxyuridine
  参考文献：
  名称：

  Palladium-mediated coupling between organic disulfides and nucleic acid constituents

  摘要：

  DOI：

  10.1021/ja00183a061

文献信息

• Palladium-mediated synthesis of C-5 pyrimidine nucleoside thioethers from disulfides and mercurinucleosides
  作者：Donald E. Bergstrom、Peter Beal、Jeffrey Jenson、Xiaoping Lin

  DOI：10.1021/jo00019a025

  日期：1991.9

  Thioether-linked side chains can be created at C-5 of pyrimidine nucleosides via a palladium-mediated reaction of mercurated nucleosides with organic disulfides. 5-(Chloromercuri)-2'-deoxyuridine reacts with butyl disulfide, phenyl disulfide, dimethyl 3,3'-dithiodipropionate, and N,N'-bis(trifluoroacetyl)cystamine to yield respectively 5-(1-thiapentyl)-2'-deoxyuridine, 5-(phenylthio)-2'-deoxyuridine, 5-[3-(methoxycarbonyl)-1-thiapropyl]-2'-deoxyuridine, and 5-[3-(trifluoroacetamido)-1-thiapropyl]-2'-deoxyuridine in yields ranging from 46 to 73%. Other mercurated nucleosides, including 5-(chloromercuri)-2'-deoxycytidine, 5-(chloromercuri)cytidine, and 5-(chloromercuri)tubercidin react with N,N'-bis(trifluoroacetyl)cystamine and lithium-palladium chloride in methanol to yield the corresponding coupled products, but the yields are much lower (5-10%). The nucleoside coupling reaction is complicated by competing side reactions between disulfides and Pd2+, which remain to be elucidated.
• BERGSTROM, DON;BEAL, PETER;HUSAIN, ADIL;LIND, ROBERT;JENSON, JEFFREY, J. AMER. CHEM. SOC., 111,(1989) N, C. 374-375
  作者：BERGSTROM, DON、BEAL, PETER、HUSAIN, ADIL、LIND, ROBERT、JENSON, JEFFREY

  DOI：——

  日期：——