methyl (2S,3S,4R,5R)-3,4-diacetyloxy-5-(6-amino-2-iodopurin-9-yl)oxolane-2-carboxylate | 1195939-18-4

• 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: methyl (2S,3S,4R,5R)-3,4-diacetyloxy-5-(6-amino-2-iodopurin-9-yl)oxolane-2-carboxylate
• CAS: 1195939-18-4
• 化学式: C₁₅H₁₆IN₅O₇
• 分子量: 505.226
• InChiKey: OBOCUDSCCDCWCL-MPXOCVNLSA-N

物化性质

• 沸点：
  661.6±65.0 °C(Predicted)
• 密度：
  2.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  158
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  methyl (2S,3S,4R,5R)-3,4-diacetyloxy-5-(6-amino-2-iodopurin-9-yl)oxolane-2-carboxylate 、 乙胺 以 四氢呋喃 为溶剂， 反应 3.0h， 以61%的产率得到2-iodo NECA
  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：

  beta-D-呋喃核糖酸甲酯三乙酸酯 、 2-碘-6-氨基嘌呤 在 硫酸氢铵 、 六甲基二硅氮烷 、 三氟甲磺酸三甲基硅酯 作用下， 以 乙腈 、 1,2-二氯乙烷 为溶剂， 反应 2.33h， 以55%的产率得到methyl (2S,3S,4R,5R)-3,4-diacetyloxy-5-(6-amino-2-iodopurin-9-yl)oxolane-2-carboxylate
  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