N,N-di(tert-butoxycarbonyl)-9-(prop-2-yn-1-yl)-9H-purin-6-amine | 308239-96-5

• 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: N,N-di(tert-butoxycarbonyl)-9-(prop-2-yn-1-yl)-9H-purin-6-amine
• 英文别名: tert-butyl N-[(2-methylpropan-2-yl)oxycarbonyl]-N-(9-prop-2-ynylpurin-6-yl)carbamate
• CAS: 308239-96-5
• 化学式: C₁₈H₂₃N₅O₄
• 分子量: 373.412
• InChiKey: HIJRONGEAHTNOP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  99.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N,N-di(tert-butoxycarbonyl)-9-(prop-2-yn-1-yl)-9H-purin-6-amine 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 N,N-di(tert-butoxycarbonyl)-9-(propa-1,2-dien-1-yl)-9H-purin-6-amine
  参考文献：
  名称：

  A New Strategy To Construct Acyclic Nucleosides via Ag(I)-Catalyzed Addition of Pronucleophiles to 9-Allenyl-9H-purines

  摘要：

  A new strategy to construct acyclic nucleosides with diverse side chains was developed. With Ag(I) salts as catalysts, the hydrocarboxylation, hydroamination, and hydrocarbonation reactions proceeded well, affording acyclic nucleosides in good yields (41 examples, 60-98% yields). Meanwhile, these reactions exhibited high chemoselectivities and E-selectivities.

  DOI：

  10.1021/ol4036566
• 作为产物：
  描述：

  腺嘌呤 在 4-二甲氨基吡啶 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 N,N-di(tert-butoxycarbonyl)-9-(prop-2-yn-1-yl)-9H-purin-6-amine
  参考文献：
  名称：

  钯催化串联环化－阴离子捕获。第6部分：1通过捕获原位生成的乙烯基锡烷来合成糖，核苷，嘌呤，苯并二氮杂pin酮和β-内酰胺类似物

  摘要：

  带有β-杂原子的炔烃的区域选择性钯催化的氢化锡烷基化主要提供α-乙烯基锡（IV）化合物，这些化合物在钯催化的环化-阴离子捕获过程中用作终止物种。附于炔部分的药效基团允许以高收率合成糖，核苷，嘌呤，苯并二氮杂酮和β-内酰胺类似物。

  DOI：

  10.1016/s0040-4020(00)00661-x

文献信息

• Design and Synthesis of Nucleoproline Amino Acids for the Straightforward Preparation of Chiral and Conformationally Constrained Nucleopeptides
  作者：Rolf A. Kramer、Konrad H. Bleicher、Helma Wennemers

  DOI：10.1002/hlca.201200557

  日期：2012.12

  A straightforward synthesis of orthogonally protected nucleoproline (Nup) amino acids and their coupling to oligomers are described. A key step is the attachment of alkynylated nucleobases to Fmoc‐protected 4‐azidoproline (Fmoc‐Azp‐OH) by a Cu‐catalyzed 1,3‐dipolar cycloaddition (‘click reaction’). The developed protocol allows preparation of the nucleoprolines in scales of >30 g. Solid‐phase peptide

  描述了正交保护的脯氨酸（Nup）氨基酸的直接合成及其与寡聚物的偶联。关键一步是通过Cu催化的1,3-偶极环加成反应将炔基化碱基与Fmoc保护的4-叠氮脯氨酸（Fmoc-Azp-OH）结合（点击反应）。所开发的方案允许制备> 30 g规模的脯氨酸。这些Nup氨基酸证明了固相肽合成非常简单。所得的寡核苷酸脯氨酸肽具有确定的螺旋，在H 2 O中的溶解性非常好，并且显示出与最近报道的α-核丙氨酸肽相当的细胞穿透特性。
• Palladium Catalysed Tandem Cyclisation–Anion Capture. Part 6: Synthesis of Sugar, Nucleoside, Purine, Benzodiazepinone and β-lactam Analogues via Capture of in situ Generated Vinylstannanes
  作者：Adele Casaschi、Ronald Grigg、José M. Sansano

  DOI：10.1016/s0040-4020(00)00661-x

  日期：2000.9

  The regioselective palladium catalysed hydrostannylation of alkynes bearing a β-heteroatom affords mainly α-vinyltin(IV) compounds that are used as terminating species in palladium catalysed cyclisation–anion capture processes. The pharmacophore attached to the alkyne moiety permits the synthesis of sugars, nucleosides, purines, benzodiazepinones and β-lactams analogues in good yields.

  带有β-杂原子的炔烃的区域选择性钯催化的氢化锡烷基化主要提供α-乙烯基锡（IV）化合物，这些化合物在钯催化的环化-阴离子捕获过程中用作终止物种。附于炔部分的药效基团允许以高收率合成糖，核苷，嘌呤，苯并二氮杂酮和β-内酰胺类似物。
• A New Strategy To Construct Acyclic Nucleosides via Ag(I)-Catalyzed Addition of Pronucleophiles to 9-Allenyl-9<i>H</i>-purines
  作者：Tao Wei、Ming-Sheng Xie、Gui-Rong Qu、Hong-Ying Niu、Hai-Ming Guo

  DOI：10.1021/ol4036566

  日期：2014.2.7

  A new strategy to construct acyclic nucleosides with diverse side chains was developed. With Ag(I) salts as catalysts, the hydrocarboxylation, hydroamination, and hydrocarbonation reactions proceeded well, affording acyclic nucleosides in good yields (41 examples, 60-98% yields). Meanwhile, these reactions exhibited high chemoselectivities and E-selectivities.