(3aR,4R,6S,6aS)-4-[6-(benzotriazol-1-yloxy)-2-iodopurin-9-yl]-N-ethyl-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole-6-carboxamide | 1195939-23-1

• 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: (3aR,4R,6S,6aS)-4-[6-(benzotriazol-1-yloxy)-2-iodopurin-9-yl]-N-ethyl-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole-6-carboxamide
• CAS: 1195939-23-1
• 化学式: C₂₁H₂₁IN₈O₅
• 分子量: 592.353
• InChiKey: KHLVNTKLANTYRR-NXEZDXNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  35
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  140
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (3aR,4R,6S,6aS)-4-[6-(benzotriazol-1-yloxy)-2-iodopurin-9-yl]-N-ethyl-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole-6-carboxamide 在 氨 作用下， 以 水 、 乙腈 为溶剂， 反应 3.0h， 以96%的产率得到2-碘-5’-乙基甲酰氨基-2’,3’-O-异丙基亚基腺苷
  参考文献：
  名称：

  Linear and convergent approaches to 2-substituted adenosine-5′-N-alkylcarboxamides

  摘要：

  Herein we report both linear and convergent pathways for the preparation of 2-alkynyl substituted adenosine-5'-N-ethylcarboxamides via the versatile synthetic intermediate, 2-iodoadenosine-5'-N-ethylcarboxamide (13). The linear approach afforded 13 in an overall yield of 30% from guanosine over eight synthetic steps. The convergent approach was shorter, but proceeded in lower yield (five steps, 20% yield). Both approaches compare favourably with previously reported syntheses of 13, which has been prepared in 15% yield from guanosine over nine steps. 2-Iodoadenosine-5'-N-ethylcarboxamide (13) was subsequently converted to HENECA (2) and PHPNECA (3) to exemplify the utility of this approach for the preparation of potent A(2A) adenosine receptor agonists. The linear approach was also amenable to the synthesis of 2-fluoropurine ribosides, which were subsequently elaborated into 2-alkylaminoadenosine-5'-N-ethylcarboxamides. Furthermore, both of these synthetic approaches are readily amenable to the synthesis of adenosine analogues with varied 2-, 6- and 5'-substitution patterns. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.08.057
• 作为产物：
  描述：

  O6-(benzotriazol-1-yl)-2',3'-O-isopropylideneguanosine-5'-N-ethylcarboxamide 在 亚硝酸特丁酯 、 二碘甲烷 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以76%的产率得到(3aR,4R,6S,6aS)-4-[6-(benzotriazol-1-yloxy)-2-iodopurin-9-yl]-N-ethyl-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole-6-carboxamide
  参考文献：
  名称：

  Linear and convergent approaches to 2-substituted adenosine-5′-N-alkylcarboxamides

  摘要：

  Herein we report both linear and convergent pathways for the preparation of 2-alkynyl substituted adenosine-5'-N-ethylcarboxamides via the versatile synthetic intermediate, 2-iodoadenosine-5'-N-ethylcarboxamide (13). The linear approach afforded 13 in an overall yield of 30% from guanosine over eight synthetic steps. The convergent approach was shorter, but proceeded in lower yield (five steps, 20% yield). Both approaches compare favourably with previously reported syntheses of 13, which has been prepared in 15% yield from guanosine over nine steps. 2-Iodoadenosine-5'-N-ethylcarboxamide (13) was subsequently converted to HENECA (2) and PHPNECA (3) to exemplify the utility of this approach for the preparation of potent A(2A) adenosine receptor agonists. The linear approach was also amenable to the synthesis of 2-fluoropurine ribosides, which were subsequently elaborated into 2-alkylaminoadenosine-5'-N-ethylcarboxamides. Furthermore, both of these synthetic approaches are readily amenable to the synthesis of adenosine analogues with varied 2-, 6- and 5'-substitution patterns. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.08.057

文献信息

• Linear and convergent approaches to 2-substituted adenosine-5′-N-alkylcarboxamides
  作者：Richard C. Foitzik、Shane M. Devine、Nicholas E. Hausler、Peter J. Scammells

  DOI：10.1016/j.tet.2009.08.057

  日期：2009.10

  Herein we report both linear and convergent pathways for the preparation of 2-alkynyl substituted adenosine-5'-N-ethylcarboxamides via the versatile synthetic intermediate, 2-iodoadenosine-5'-N-ethylcarboxamide (13). The linear approach afforded 13 in an overall yield of 30% from guanosine over eight synthetic steps. The convergent approach was shorter, but proceeded in lower yield (five steps, 20% yield). Both approaches compare favourably with previously reported syntheses of 13, which has been prepared in 15% yield from guanosine over nine steps. 2-Iodoadenosine-5'-N-ethylcarboxamide (13) was subsequently converted to HENECA (2) and PHPNECA (3) to exemplify the utility of this approach for the preparation of potent A(2A) adenosine receptor agonists. The linear approach was also amenable to the synthesis of 2-fluoropurine ribosides, which were subsequently elaborated into 2-alkylaminoadenosine-5'-N-ethylcarboxamides. Furthermore, both of these synthetic approaches are readily amenable to the synthesis of adenosine analogues with varied 2-, 6- and 5'-substitution patterns. (c) 2009 Elsevier Ltd. All rights reserved.