N-(7-methyl-1H-imidazo[4,5-c]pyridin-4-yl)-2,2,3,3-tetramethylsuccinimide | 1202405-84-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 英文名称: N-(7-methyl-1H-imidazo[4,5-c]pyridin-4-yl)-2,2,3,3-tetramethylsuccinimide
• 英文别名: 2,5-Pyrrolidinedione,3,3,4,4-tetramethyl-1-(7-methyl-3h-imidazo[4,5-c]pyridin-4-yl)-；3,3,4,4-tetramethyl-1-(7-methyl-3H-imidazo[4,5-c]pyridin-4-yl)pyrrolidine-2,5-dione
• CAS: 1202405-84-2
• 化学式: C₁₅H₁₈N₄O₂
• 分子量: 286.334
• InChiKey: FYNXSXUQTRSDQU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  79
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(7-methyl-1H-imidazo[4,5-c]pyridin-4-yl)-2,2,3,3-tetramethylsuccinimide 在 4-二甲氨基吡啶 、 二碳酸二叔丁酯 、 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 、 sodium acetate 作用下， 以 二氯甲烷 、 四氯化碳 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.25h， 生成
  参考文献：
  名称：

  Tetramethylsuccinimide as a Directing/Protecting Group in Purine Glycosylations

  摘要：

  Tetra methylsuccinic anhydride can be used to protect the exocyclic amine of 6-aminopurine derivatives by forming the corresponding tetramethysuccinimide. X-ray crystallography confirms that the imide carbonyl and the methyl groups are positioned to sterically block the N7 nitrogen so that glycosylations occur with very high regiochemical control at N9. This approach Is particularly effective for 3-substituted purines where the substituent tends to block access to N9 and inhibit glycosylation at that site.

  DOI：

  10.1021/ol9025028
• 作为产物：
  描述：

  3,3,4,4-四甲基四氢呋喃-2,5-二酮 、 7-甲基-1H-咪唑并[4,5-C]吡啶-4-胺 在 吡啶 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 氯化亚砜 作用下， 反应 20.0h， 以81%的产率得到N-(7-methyl-1H-imidazo[4,5-c]pyridin-4-yl)-2,2,3,3-tetramethylsuccinimide
  参考文献：
  名称：

  Tetramethylsuccinimide as a Directing/Protecting Group in Purine Glycosylations

  摘要：

  Tetra methylsuccinic anhydride can be used to protect the exocyclic amine of 6-aminopurine derivatives by forming the corresponding tetramethysuccinimide. X-ray crystallography confirms that the imide carbonyl and the methyl groups are positioned to sterically block the N7 nitrogen so that glycosylations occur with very high regiochemical control at N9. This approach Is particularly effective for 3-substituted purines where the substituent tends to block access to N9 and inhibit glycosylation at that site.

  DOI：

  10.1021/ol9025028

文献信息

• 2,3-Dicyclohexylsuccinimide as a directing/protecting group for the regioselective glycosylation or alkylation of purines
  作者：Ayan Pal、Kerry J. Salandria、Joseph W. Arico、Mark K. Schlegel、Larry W. McLaughlin

  DOI：10.1039/c3cc37265k

  日期：——

  Here we describe the synthesis and application of a novel 2,3-dicyclohexylsuccinimide (Cy2SI) protecting group towards regioselective purine glycosylation and alkylation reactions. This bulky protecting group promotes high regioselectivity during the glycosylation (as well as diastereoselectivity) or alkylation of purines using Hoffer's chlorosugar or tert-butyl bromoacetate, respectively. Cy2SI offers the additional synthetic advantage that other base-labile protecting groups, such as toluoyl esters, can be selectively removed in its presence without affecting the imide.

  在此，我们介绍了一种新型 2,3-二环己基琥珀酰亚胺（Cy2SI）保护基团的合成及其在区域选择性嘌呤糖基化和烷基化反应中的应用。在分别使用 Hoffer's 氯糖或溴乙酸叔丁酯对嘌呤进行糖基化（以及非对映选择性）或烷基化反应时，这种笨重的保护基团可提高区域选择性。Cy2SI 还具有额外的合成优势，即在其存在下可选择性地去除甲苯甲酰酯等其他碱基不敏感的保护基团，而不会影响亚胺。