S,S'-bis(2-nitrophenylsulfanyl)-3',5'-dithio-2'-deoxy-α-4-N-n-octanoyladenosine | 491837-18-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: S,S'-bis(2-nitrophenylsulfanyl)-3',5'-dithio-2'-deoxy-α-4-N-n-octanoyladenosine
• 英文别名: N-[9-[(2S,4S,5R)-4-[(2-nitrophenyl)disulfanyl]-5-[[(2-nitrophenyl)disulfanyl]methyl]oxolan-2-yl]purin-6-yl]octanamide
• CAS: 491837-18-4
• 化学式: C₃₀H₃₃N₇O₆S₄
• 分子量: 715.899
• InChiKey: QPNPTUIXODPQDL-PWMMPXSUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  47
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  275
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  S,S'-bis(2-nitrophenylsulfanyl)-3',5'-dithio-2'-deoxy-α-4-N-n-octanoyladenosine 在 三乙胺 、 甲胺 、 乙硫醇 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 3',5'-dithio-2'-deoxy-α-adenosine
  参考文献：
  名称：

  Artificial Nucleosides Possessing Metal Binding Sites at the 3‘- and 5‘-Positions of the Deoxyribose Moieties

  摘要：

  This paper describes a convenient synthetic procedure for nucleoside mimics, 1-6, in which the 3',5'-hydroxy groups of natural 2'-deoxythymidine or 2'-deoxyadenosine are replaced by thiol, amine, or alkylthiol groups. Such nucleosides would be built up into a single DNA strand with cooperative participation of metal coordination, where internucleoside linkages are replaced by metal complexation motifs. The X-ray crystal structure and complexation behaviors of 3',5'-dithiothymidine, 1, with Au-I are also reported.

  DOI：

  10.1021/jo026026l
• 作为产物：
  描述：

  N-(7H-嘌呤-6-基)辛酰胺 、 3',5'-S-bis(2-nitrophenylsulfanyl)-3',5'-dithiothymidine 在 三甲基氯硅烷 、 六甲基二硅氮烷 、 三氟甲磺酸三甲基硅酯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 以42%的产率得到S,S'-bis(2-nitrophenylsulfanyl)-3',5'-dithio-2'-deoxy-β-4-N-n-octanoyladenosine
  参考文献：
  名称：

  Artificial Nucleosides Possessing Metal Binding Sites at the 3‘- and 5‘-Positions of the Deoxyribose Moieties

  摘要：

  This paper describes a convenient synthetic procedure for nucleoside mimics, 1-6, in which the 3',5'-hydroxy groups of natural 2'-deoxythymidine or 2'-deoxyadenosine are replaced by thiol, amine, or alkylthiol groups. Such nucleosides would be built up into a single DNA strand with cooperative participation of metal coordination, where internucleoside linkages are replaced by metal complexation motifs. The X-ray crystal structure and complexation behaviors of 3',5'-dithiothymidine, 1, with Au-I are also reported.

  DOI：

  10.1021/jo026026l

文献信息

• Artificial Nucleosides Possessing Metal Binding Sites at the 3‘- and 5‘-Positions of the Deoxyribose Moieties
  作者：Jun-ya Chiba、Kentaro Tanaka、Yukinori Ohshiro、Ryosuke Miyake、Shuichi Hiraoka、Motoo Shiro、Mitsuhiko Shionoya

  DOI：10.1021/jo026026l

  日期：2003.1.1

  This paper describes a convenient synthetic procedure for nucleoside mimics, 1-6, in which the 3',5'-hydroxy groups of natural 2'-deoxythymidine or 2'-deoxyadenosine are replaced by thiol, amine, or alkylthiol groups. Such nucleosides would be built up into a single DNA strand with cooperative participation of metal coordination, where internucleoside linkages are replaced by metal complexation motifs. The X-ray crystal structure and complexation behaviors of 3',5'-dithiothymidine, 1, with Au-I are also reported.