N2-Boc-9-([1'S,2'S,5'R]-2'-isopropyl-5'-methylcyclohexyl)-6-chloro-9H-purin-2-ylamine | 1236151-79-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: N2-Boc-9-([1'S,2'S,5'R]-2'-isopropyl-5'-methylcyclohexyl)-6-chloro-9H-purin-2-ylamine
• CAS: 1236151-79-3
• 化学式: C₂₀H₃₀ClN₅O₂
• 分子量: 407.944
• InChiKey: OSUALFMUEJGHGB-RDBSUJKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.46
• 重原子数：
  28.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  81.93
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  N2-Boc-9-([1'S,2'S,5'R]-2'-isopropyl-5'-methylcyclohexyl)-6-chloro-9H-purin-2-ylamine 在 甲酸 作用下， 以 水 为溶剂， 反应 2.0h， 以96%的产率得到2-amino-9-([1'S,2'S,5'R]-2'-isopropyl-5'-methylcyclohexyl)-1,9-dihydro-purin-6-one
  参考文献：
  名称：

  Concise access to N9-mono-, N2-mono- and N2,N9-di-substituted guanines via efficient Mitsunobu reactions

  摘要：

  Guanine poses several problems to the synthetic chemist owing to its polyfunctional nature and poor solubility. Over the past few decades, synthetic guanines have found applications as anti-cancer and anti-viral agents. Coupled with the ever-growing interest in designer PNAs and G-quartets, simple and efficient synthetic routes to novel guanines would be of significant benefit. We herein report that, upon simple protection and/or activation step(s), the guanine precursor 2-amino-6-chloropurine is rendered an excellent substrate for Mitsunobu chemistry, furnishing, after subsequent hydrolytic dechlorination and appropriate deprotection step(s), the desired N9-mono-, N2-mono- or N2,N9-di-substituted guanines in excellent yields (>= 80%). Importantly, we demonstrate that N9-functionalization proceeds with very good N9/N7 regioselectivity and with complete inversion of stereochemistry. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.03.118
• 作为产物：
  描述：

  L-薄荷醇 、 tert-butyl (6-chloro-9H-purin-2-yl)carbamate 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 0.3h， 以92%的产率得到N2-Boc-9-([1'S,2'S,5'R]-2'-isopropyl-5'-methylcyclohexyl)-6-chloro-9H-purin-2-ylamine
  参考文献：
  名称：

  Concise access to N9-mono-, N2-mono- and N2,N9-di-substituted guanines via efficient Mitsunobu reactions

  摘要：

  Guanine poses several problems to the synthetic chemist owing to its polyfunctional nature and poor solubility. Over the past few decades, synthetic guanines have found applications as anti-cancer and anti-viral agents. Coupled with the ever-growing interest in designer PNAs and G-quartets, simple and efficient synthetic routes to novel guanines would be of significant benefit. We herein report that, upon simple protection and/or activation step(s), the guanine precursor 2-amino-6-chloropurine is rendered an excellent substrate for Mitsunobu chemistry, furnishing, after subsequent hydrolytic dechlorination and appropriate deprotection step(s), the desired N9-mono-, N2-mono- or N2,N9-di-substituted guanines in excellent yields (>= 80%). Importantly, we demonstrate that N9-functionalization proceeds with very good N9/N7 regioselectivity and with complete inversion of stereochemistry. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.03.118