9-(3'-azido-2',3',5'-trideoxy-5'-(trimethylsilyl)ethynyl-β-D-ribofuranosyl)-6-octanoyladenine | 1226527-97-4

• 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: 9-(3'-azido-2',3',5'-trideoxy-5'-(trimethylsilyl)ethynyl-β-D-ribofuranosyl)-6-octanoyladenine
• 英文别名: N-[9-[(2R,4S,5R)-4-azido-5-(3-trimethylsilylprop-2-ynyl)oxolan-2-yl]purin-6-yl]octanamide
• CAS: 1226527-97-4
• 化学式: C₂₃H₃₄N₈O₂Si
• 分子量: 482.661
• InChiKey: FLMJIANJJOLQJG-NLWGTHIKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.36
• 重原子数：
  34
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  96.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  9-(3'-azido-2',3',5'-trideoxy-5'-(trimethylsilyl)ethynyl-β-D-ribofuranosyl)-6-octanoyladenine 在 甲醇 、 ammonium hydroxide 作用下， 以 水 为溶剂， 反应 2.0h， 以87%的产率得到9-(3'-azido-5'-ethynyl-2',3',5',-trideoxy-β-D-ribofuranosyl)adenine
  参考文献：
  名称：

  Synthesis and structures of deoxyribonucleoside analogues for triazole-linked DNA (TLDNA)

  摘要：

  Deoxyribonucleoside analogues bearing acetylene group at the pseudo-5'-position and azido group at the pseudo-3'-position have been synthesized by transglycosylation reaction of deoxythymidine analogue with adenine, cytosine, and guanine nucleobases as nucleophiles. The structures of analogues were studied in crystalline state by X-ray crystallography as well as in solution phase by NMR spectroscopy and showed the puckering conformations similar to the natural congeners. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.02.046
• 作为产物：
  描述：

  3'-azido-2',3',5'-trideoxy-5'-(trimethylsilyl)ethynylthymidine 、 N-(6,7-二氢-6-氧代-1H-嘌呤-2-基)-2-甲基丙酰胺 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 1,2-二氯乙烷 为溶剂， 反应 10.0h， 以31%的产率得到9-(3'-azido-2',3',5'-trideoxy-5'-(trimethylsilyl)ethynyl-α-D-ribofuranosyl)-2-isobutyrylguanine
  参考文献：
  名称：

  Synthesis and structures of deoxyribonucleoside analogues for triazole-linked DNA (TLDNA)

  摘要：

  Deoxyribonucleoside analogues bearing acetylene group at the pseudo-5'-position and azido group at the pseudo-3'-position have been synthesized by transglycosylation reaction of deoxythymidine analogue with adenine, cytosine, and guanine nucleobases as nucleophiles. The structures of analogues were studied in crystalline state by X-ray crystallography as well as in solution phase by NMR spectroscopy and showed the puckering conformations similar to the natural congeners. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.02.046