8-aza-7-deaza-7-propynyladenosine

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 吡唑并[3，4-d]嘧啶糖苷
• 英文名称: 8-aza-7-deaza-7-propynyladenosine
• 英文别名: 4-amino-3-propynyl-1-(β-D-ribofuranosyl)-1H-pyrazolo[3,4-d]pyrimidine；(2R,3R,4S,5R)-2-(4-amino-3-prop-1-ynylpyrazolo[3,4-d]pyrimidin-1-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• 化学式: C₁₃H₁₅N₅O₄
• 分子量: 305.293
• InChiKey: BNRYGJMZKGFKOA-QYVSTXNMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  140
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  7-iodo-8-aza-7-deazaadenosine 、 丙炔 在 四(三苯基膦)钯 copper(l) iodide 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以47%的产率得到8-aza-7-deaza-7-propynyladenosine
  参考文献：
  名称：

  8-Aza-7-deaza-7-propynyladenosine methanol solvate

  摘要：

  In the title compound, 4-amino-3-propynyl-1-(beta-D-ribofuranosyl)-1H-pyrazolo[3,4-d] pyrimidine methanol solvate, C13H15N5O4 center dot CH3OH, the torsion angle of the N-glycosylic bond is between anti and high-anti [chi =-101.8 (5)degrees]. The ribofuranose moiety adopts the C3'-endo (T-3(2)) sugar conformation (N-type) and the conformation at the exocyclic C-C bond is+sc (gauche, gauche). The propynyl group is out of the plane of the nucleobase and is bent. The compound forms a three-dimensional network which is stabilized by several hydrogen bonds (O-H center dot center dot center dot O and O-H center dot center dot center dot N). The nucleobases are stacked head-to-tail. The methanol solvent molecule forms hydrogen bonds with both the nucleobase and the sugar moiety.

  DOI：

  10.1107/s0108270105001927

文献信息

• 8-Aza-7-deaza-7-propynyladenosine methanol solvate
  作者：Wenqing Lin、Kuiying Xu、Henning Eickmeier、Frank Seela

  DOI：10.1107/s0108270105001927

  日期：2005.4.15

  In the title compound, 4-amino-3-propynyl-1-(beta-D-ribofuranosyl)-1H-pyrazolo[3,4-d] pyrimidine methanol solvate, C13H15N5O4 center dot CH3OH, the torsion angle of the N-glycosylic bond is between anti and high-anti [chi =-101.8 (5)degrees]. The ribofuranose moiety adopts the C3'-endo (T-3(2)) sugar conformation (N-type) and the conformation at the exocyclic C-C bond is+sc (gauche, gauche). The propynyl group is out of the plane of the nucleobase and is bent. The compound forms a three-dimensional network which is stabilized by several hydrogen bonds (O-H center dot center dot center dot O and O-H center dot center dot center dot N). The nucleobases are stacked head-to-tail. The methanol solvent molecule forms hydrogen bonds with both the nucleobase and the sugar moiety.
• 7-SUBSTITUTED 8-AZA-7-DEAZAPURINES AND 2,8-DIAZA-7-DEAZA-PURINES: SYNTHESIS OF NUCLEOSIDES AND OLIGONUCLEOTIDES
  作者：Wenqing Lin、Kuiying Xu、Frank Seela

  DOI：10.1081/ncn-200059218

  日期：2005.4.1

  7-Substituted 8-aza-7-deazaadenosines la-e were synthesized by Sonogashira cross coupling from the corresponding 7-iodo nucleoside in 36- 79% yields. Starting from 7-bromo (or 7-iodo)-8-aza- 7-deazaadenine, 2a,b were obtained by acid-catalyzed glycosylation followed by deprotection in 53 and 35% yields, respectively. Compounds 2b was applied to cross coupling reaction to give 2c-d in 34-95% yield. Compounds 2a and 4b were further transformed to the phosphoramidites 5 and 6b in 9 and 49% overall yields, which were incorporated into oligonucleotides.