5-<3-(Trifluoroacetamido)-1-thiapropyl>-2'-deoxyuridine | 118042-45-8

• 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-<3-(Trifluoroacetamido)-1-thiapropyl>-2'-deoxyuridine
• 英文别名: 5-[3-(Trifluoroacetamido)-1-thiapropyl]-2'-deoxyuridine；2,2,2-trifluoro-N-[2-[1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2,4-dioxopyrimidin-5-yl]sulfanylethyl]acetamide
• CAS: 118042-45-8
• 化学式: C₁₃H₁₆F₃N₃O₆S
• 分子量: 399.348
• InChiKey: UBBBHFHNNCVGBY-LKEWCRSYSA-N

物化性质

• 密度：
  1.63±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  154
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  5-<3-(Trifluoroacetamido)-1-thiapropyl>-2'-deoxyuridine 在 吡啶 、 氨 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 30.5h， 生成 5'-O--5-<<2-<<2-<<(2,2-dimethylethoxy)carbonyl>amino>-3-<1-<(2,2-dimethylethoxy)carbonyl>-1H-imidazol-4-yl>-1-oxopropyl>amino>ethyl>thio>-2'-deoxyuridine
  参考文献：
  名称：

  Synthesis and characterization of nucleoside peptides: toward chemical ribonucleases. 1

  摘要：

  DOI：

  10.1021/jo00304a026
• 作为产物：
  描述：

  5-(chloromercuri)-2'-deoxyuridine 、 N,N'-Bis(trifluoroacetyl)cystamine 在 lithium tetrachloropalladate 作用下， 以 甲醇 为溶剂， 以51%的产率得到5-<3-(Trifluoroacetamido)-1-thiapropyl>-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

• Synthesis of oligonucleotides containing N2-(5-carboxypentyl)-2′-deoxyguanosine and 5-[2-(4′-methyl-2,2′-dipyrid-4-yl-carboxamido)ethylthio]-2′-deoxyuridine
  作者：Guangyi Wang、Donald E. Bergstrom

  DOI：10.1016/s0040-4039(00)61684-2

  日期：1993.10

  Synthesis of 2′-deoxyguanosine tethered at N-2 to a carboxypentyl group and 2′-deoxyuridine tethered through C-5 to a bipyridine is described. The modified nucleosides were converted to the corresponding phosphoramidites and incorporated into mono- and di-modified oligonucleotides. The carboxypentyl group was introduced in the ester form into oligonucleotides and recovered by hydrolysis with aqueous

  描述了在N-2处被束缚到羧基戊基的2'-脱氧鸟苷和通过C-5被束缚到联吡啶的2'-脱氧尿苷的合成。将修饰的核苷转化为相应的亚磷酰胺，并掺入单修饰和双修饰的寡核苷酸中。将羧基戊基以酯的形式引入寡核苷酸中，并通过用三乙胺水溶液水解来回收。
• 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：——