methyl 2',3'-O-isopropylideneguanosine-5'-carboxylate | 1195939-21-9

• 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 2',3'-O-isopropylideneguanosine-5'-carboxylate
• 英文别名: methyl (3aR,4R,6S,6aS)-4-(2-amino-6-oxo-1H-purin-9-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole-6-carboxylate
• CAS: 1195939-21-9
• 化学式: C₁₄H₁₇N₅O₆
• 分子量: 351.319
• InChiKey: IATKHOHGVPYOQF-MCHASIABSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  139
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 2',3'-O-isopropylideneguanosine-5'-carboxylate 在 盐酸 、 水 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 、 乙腈 、 叔丁醇 为溶剂， 反应 21.0h， 生成 2-amino-N⁶-ethyladenosine-5’-N-methylcarboxamide
  参考文献：
  名称：

  Design, synthesis and evaluation of N⁶-substituted 2-aminoadenosine-5′-N-methylcarboxamides as A₃ adenosine receptor agonists

  摘要：

  一系列N6-取代2-氨基腺苷-5'-N-甲基羧酰胺从多功能中间体O6-(苯并三唑-1-基)-2-氨基-2',3'-O-异丙基葡萄糖苷-5'-N-甲基羧酰胺（1）合成，并作为A3腺苷受体激动剂进行评价。

  DOI：

  10.1039/c3md00364g
• 作为产物：
  描述：

  2',3'-O-异丙亚基鸟苷 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 氯化亚砜 、 碘苯二乙酸 作用下， 以 水 、 乙腈 为溶剂， 反应 32.0h， 生成 methyl 2',3'-O-isopropylideneguanosine-5'-carboxylate
  参考文献：
  名称：

  Design, synthesis and evaluation of N⁶-substituted 2-aminoadenosine-5′-N-methylcarboxamides as A₃ adenosine receptor agonists

  摘要：

  一系列N6-取代2-氨基腺苷-5'-N-甲基羧酰胺从多功能中间体O6-(苯并三唑-1-基)-2-氨基-2',3'-O-异丙基葡萄糖苷-5'-N-甲基羧酰胺（1）合成，并作为A3腺苷受体激动剂进行评价。

  DOI：

  10.1039/c3md00364g

文献信息

• Synthesis and Utility of 2-Halo-O6-(benzotriazol-1-yl)-Functionalized Purine Nucleosides
  作者：Shane M. Devine、Peter J. Scammells

  DOI：10.1002/ejoc.201001395

  日期：2011.2

  An efficient synthesis of 2-halo-O6-(benzotriazol-1-yl)-substituted purine nucleosides has been accomplished via (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP)-mediated coupling and subsequent halogenation via diazotization of the 2-amino group of various protected guanosines and directly from guanosine itself. These products are amenable to substitution and coupling

  2-卤代-O6-(苯并三唑-1-基)-取代的嘌呤核苷的有效合成是通过(苯并三唑-1-基氧基)三(二甲氨基)鏻六氟磷酸(BOP)介导的偶联和随后通过重氮化的卤化完成的各种受保护鸟苷的 2-氨基，直接来自鸟苷本身。这些产品适合在 2 位和 6 位进行取代和偶联反应，因此可以有效地获得高度官能化的嘌呤核苷。
• 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.
• Design, synthesis and evaluation of N⁶-substituted 2-aminoadenosine-5′-N-methylcarboxamides as A₃ adenosine receptor agonists
  作者：Shane M. Devine、Lauren T. May、Peter J. Scammells

  DOI：10.1039/c3md00364g

  日期：——

  A series of N⁶-substituted 2-aminoadenosine-5′-N-methylcarboxamides were synthesized from the versatile intermediate, O⁶-(benzotriazol-1-yl)-2-amino-2′,3′-O-isopropylideneinosine-5′-N-methylcarboxamide (1) and evaluated as A₃ adenosine receptor agonists.

  一系列N6-取代2-氨基腺苷-5'-N-甲基羧酰胺从多功能中间体O6-(苯并三唑-1-基)-2-氨基-2',3'-O-异丙基葡萄糖苷-5'-N-甲基羧酰胺（1）合成，并作为A3腺苷受体激动剂进行评价。