8-vinyl-9-[2,3-di-O-(tert-butyldimethylsilyl)-β-D-ribo-pentofuranosyl]-adenine | 620597-40-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 8-vinyl-9-[2,3-di-O-(tert-butyldimethylsilyl)-β-D-ribo-pentofuranosyl]-adenine
• 英文别名: [(2R,3R,4R,5R)-5-(6-amino-8-ethenylpurin-9-yl)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]oxolan-2-yl]methanol
• CAS: 620597-40-2
• 化学式: C₂₄H₄₃N₅O₄Si₂
• 分子量: 521.808
• InChiKey: QTOVASPRYSEDOY-CIVUBGFFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.72
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  118
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  8-vinyl-9-[2,3-di-O-(tert-butyldimethylsilyl)-β-D-ribo-pentofuranosyl]-adenine 在 氢氟酸 、 甲基锂 作用下， 以 四氢呋喃 、 乙醚 、 乙腈 为溶剂， 反应 24.0h， 生成 8-vinyl-9-(5-O-tosyl-β-D-ribo-pentofuranosyl)-adenine
  参考文献：
  名称：

  Synthesis of 8-vinyladenosine 5′-di- and 5′-triphosphate: evaluation of the diphosphate compound on ribonucleotide reductase

  摘要：

  The synthesis of 5'-di- and 5'-triphosphate of 8-vinyladenosine to be tested on ribonucleotide reductases requires the modification of known methods. The phosphate group was introduced by treatment with an in situ generated chlorophosphite. Protection of the 2',3' diol with acetyl groups suppressed depurination during acid removal of the phosphotriester protecting groups. The di- and triphosphate compounds were obtained by treatment of the activated adenylic acid with phosphate or pyrophosphate anions followed by removal of the acetate protecting groups. Preliminary studies were conducted on Escherichia coli ribonucleotide reductase and have shown that the diphosphate compound is efficiently reduced. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)01151-7
• 作为产物：
  描述：

  8-ethenyl-2',3',5'-tris-O-(tert-butyldimethylsilyl)adenosine 在 水 、 三氟乙酸 作用下， 以78%的产率得到8-vinyl-9-[2,3-di-O-(tert-butyldimethylsilyl)-β-D-ribo-pentofuranosyl]-adenine
  参考文献：
  名称：

  Synthesis of 8-vinyladenosine 5′-di- and 5′-triphosphate: evaluation of the diphosphate compound on ribonucleotide reductase

  摘要：

  The synthesis of 5'-di- and 5'-triphosphate of 8-vinyladenosine to be tested on ribonucleotide reductases requires the modification of known methods. The phosphate group was introduced by treatment with an in situ generated chlorophosphite. Protection of the 2',3' diol with acetyl groups suppressed depurination during acid removal of the phosphotriester protecting groups. The di- and triphosphate compounds were obtained by treatment of the activated adenylic acid with phosphate or pyrophosphate anions followed by removal of the acetate protecting groups. Preliminary studies were conducted on Escherichia coli ribonucleotide reductase and have shown that the diphosphate compound is efficiently reduced. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)01151-7

文献信息

• Synthesis of 8-vinyladenosine 5′-di- and 5′-triphosphate: evaluation of the diphosphate compound on ribonucleotide reductase
  作者：Pascal Lang、Catherine Gerez、Denis Tritsch、Marc Fontecave、Jean-François Biellmann、Alain Burger

  DOI：10.1016/s0040-4020(03)01151-7

  日期：2003.9

  The synthesis of 5'-di- and 5'-triphosphate of 8-vinyladenosine to be tested on ribonucleotide reductases requires the modification of known methods. The phosphate group was introduced by treatment with an in situ generated chlorophosphite. Protection of the 2',3' diol with acetyl groups suppressed depurination during acid removal of the phosphotriester protecting groups. The di- and triphosphate compounds were obtained by treatment of the activated adenylic acid with phosphate or pyrophosphate anions followed by removal of the acetate protecting groups. Preliminary studies were conducted on Escherichia coli ribonucleotide reductase and have shown that the diphosphate compound is efficiently reduced. (C) 2003 Elsevier Ltd. All rights reserved.