2',5'-bis-O-(tert-butyldimethylsilyl)-4'-cyanocordycepin | 1016648-33-1

• 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: 2',5'-bis-O-(tert-butyldimethylsilyl)-4'-cyanocordycepin
• 英文别名: (2R,4R,5R)-5-(6-aminopurin-9-yl)-4-[tert-butyl(dimethyl)silyl]oxy-2-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolane-2-carbonitrile
• CAS: 1016648-33-1
• 化学式: C₂₃H₄₀N₆O₃Si₂
• 分子量: 504.78
• InChiKey: YGZHYBJSUFVHTA-AYPBNUJASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.0
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  121
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  (4R,5R)-5-(6-amino-9H-purin-9-yl)-4-((tert-butyldimethylsilyl)oxy)-2-(((tert-butyldimethylsilyl)oxy)methyl)tetrahydrofuran-2-yl benzoate 、 三甲基氰硅烷 在 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以58%的产率得到2',5'-bis-O-(tert-butyldimethylsilyl)-4'-cyanocordycepin
  参考文献：
  名称：

  Synthesis of 4′-benzoyloxycordycepin from adenosine

  摘要：

  With an aim to synthesize 4'-substituted cordycepins, the 4'-benzoyloxy precursor (9) was prepared from adenosine through an electrophilic addition (iodo-benzoyloxylation) to the 4',5'-unsaturated derivative (5) and subsequent radical-mediated removal of the 3'-iodine atom of the resulting adducts (6). Usefulness of 9 was briefly verified by synthesizing the 4'-allyl (12) and 4'-cyano (13) analogues of cordycepin. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.01.018

文献信息

• Synthesis of 4′-benzoyloxycordycepin from adenosine
  作者：Yutaka Kubota、Mayumi Kunikata、Nobuhide Ishizaki、Kazuhiro Haraguchi、Yuki Odanaka、Hiromichi Tanaka

  DOI：10.1016/j.tet.2008.01.018

  日期：2008.3

  With an aim to synthesize 4'-substituted cordycepins, the 4'-benzoyloxy precursor (9) was prepared from adenosine through an electrophilic addition (iodo-benzoyloxylation) to the 4',5'-unsaturated derivative (5) and subsequent radical-mediated removal of the 3'-iodine atom of the resulting adducts (6). Usefulness of 9 was briefly verified by synthesizing the 4'-allyl (12) and 4'-cyano (13) analogues of cordycepin. (C) 2008 Elsevier Ltd. All rights reserved.