9-[2,5-bis-O-(tert-butyldimethylsilyl)-3-deoxy-3-iodo-4-pivaloyloxy-α-L-lyxofuranosyl]adenine | 1016648-25-1

• 分子结构分类: 有机化合物
• 英文名称: 9-[2,5-bis-O-(tert-butyldimethylsilyl)-3-deoxy-3-iodo-4-pivaloyloxy-α-L-lyxofuranosyl]adenine
• 英文别名: [(2R,3S,4S,5R)-5-(6-aminopurin-9-yl)-4-[tert-butyl(dimethyl)silyl]oxy-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-iodooxolan-2-yl] 2,2-dimethylpropanoate
• CAS: 1016648-25-1
• 化学式: C₂₇H₄₈IN₅O₅Si₂
• 分子量: 705.784
• InChiKey: KGMXSBXXLNPOCC-KAOQQYIPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.44
• 重原子数：
  40
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  124
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  9-[2,5-bis-O-(tert-butyldimethylsilyl)-3-deoxy-3-iodo-4-pivaloyloxy-α-L-lyxofuranosyl]adenine 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 以74%的产率得到9-[2,5-bis-O-(tert-butyldimethylsilyl)-3-deoxy-4-pivaloyloxy-α-L-lyxofuranosyl]adenine
  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
• 作为产物：
  描述：

  9-[2,5-bis-O-(tert-butyldimethylsilyl)-3-deoxy-β-D-glyceropent-3-enofuranosyl]adenine 、 三甲基乙酸 在 N-碘代丁二酰亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 生成 2',5'-bis-O-(tert-butyldimethylsilyl)-3'-deoxy-3'-iodo-4'-pivaloyloxyadenosine 、 9-[2,5-bis-O-(tert-butyldimethylsilyl)-3-deoxy-3-iodo-4-pivaloyloxy-α-L-lyxofuranosyl]adenine
  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