(E)-6'-bromo-(5'-deoxy-5'-methylidene)thymidine | 375352-47-9

• 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: (E)-6'-bromo-(5'-deoxy-5'-methylidene)thymidine
• 英文别名: 1-[(2R,4S,5R)-5-[(E)-2-bromoethenyl]-4-hydroxyoxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 375352-47-9
• 化学式: C₁₁H₁₃BrN₂O₄
• 分子量: 317.139
• InChiKey: TVYYPBVLCNBYII-NSVNRLROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  78.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-6'-bromo-(5'-deoxy-5'-methylidene)thymidine 在 四氮唑 、 1,1'-双(二苯基膦)二茂铁 、 palladium diacetate 、 methyloxirane 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 5'-O-(4,4'-dimethoxytrityl)thymidinyl 2-cyanoethylphosphono-[3'(O)->5'(C)]-(5'-deoxy-5'-methylidene)thymidine-3'-O-(N,N-diisopropylamino-2-cyanoethyl) phosphoramidite
  参考文献：
  名称：

  Commercially Available 5‘-DMT Phosphoramidites as Reagents for the Synthesis of Vinylphosphonate-Linked Oligonucleic Acids

  摘要：

  [GRAPHICS]Commercially available cyanoethyl phosphoramidites derived from T, d(C), d(A), and d(G) were hydrolyzed (1H-tetrazole, MeCN/H2O) to give the corresponding H-phosphonates in excellent yields. Palladium(0)-catalyzed cross-coupling of each of these with the thymidine-derived vinylbromide 2 afforded the corresponding vinylphosphonate-linked dimers T*T, d(C)*T, d(A)*T, and d(G)*T in modest to good yields. The T*T dimer was further elaborated to give a 5'-DMT-T*T-3'-CEP building block, and this was used in the automated synthesis of the TpT*TpT tetramer.

  DOI：

  10.1021/ol0166045
• 作为产物：
  描述：

  1-(2-deoxy-3-O-tert-butyldiphenylsilyl-β-D-erythro-pentadialdo-1,4-furanosyl)-5-methyluracil 在 亚磷酸氢二甲酯 、 四丁基氟化铵 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.33h， 生成 (E)-6'-bromo-(5'-deoxy-5'-methylidene)thymidine
  参考文献：
  名称：

  Commercially Available 5‘-DMT Phosphoramidites as Reagents for the Synthesis of Vinylphosphonate-Linked Oligonucleic Acids

  摘要：

  [GRAPHICS]Commercially available cyanoethyl phosphoramidites derived from T, d(C), d(A), and d(G) were hydrolyzed (1H-tetrazole, MeCN/H2O) to give the corresponding H-phosphonates in excellent yields. Palladium(0)-catalyzed cross-coupling of each of these with the thymidine-derived vinylbromide 2 afforded the corresponding vinylphosphonate-linked dimers T*T, d(C)*T, d(A)*T, and d(G)*T in modest to good yields. The T*T dimer was further elaborated to give a 5'-DMT-T*T-3'-CEP building block, and this was used in the automated synthesis of the TpT*TpT tetramer.

  DOI：

  10.1021/ol0166045

文献信息

• Commercially Available 5‘-DMT Phosphoramidites as Reagents for the Synthesis of Vinylphosphonate-Linked Oligonucleic Acids
  作者：Sahar Abbas、Richard D. Bertram、Christopher J. Hayes

  DOI：10.1021/ol0166045

  日期：2001.10.1

  [GRAPHICS]Commercially available cyanoethyl phosphoramidites derived from T, d(C), d(A), and d(G) were hydrolyzed (1H-tetrazole, MeCN/H2O) to give the corresponding H-phosphonates in excellent yields. Palladium(0)-catalyzed cross-coupling of each of these with the thymidine-derived vinylbromide 2 afforded the corresponding vinylphosphonate-linked dimers T*T, d(C)*T, d(A)*T, and d(G)*T in modest to good yields. The T*T dimer was further elaborated to give a 5'-DMT-T*T-3'-CEP building block, and this was used in the automated synthesis of the TpT*TpT tetramer.