(2R,3S,4S,5R)-2-(acetoxymethyl)-5-(2-amino-6-phenyl-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate | 236755-48-9

• 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: (2R,3S,4S,5R)-2-(acetoxymethyl)-5-(2-amino-6-phenyl-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate
• 英文别名: 2-amino-6-phenyl-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine；9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-2-amino-6-phenylpurine；[(2R,3R,4R,5R)-3,4-diacetyloxy-5-(2-amino-6-phenylpurin-9-yl)oxolan-2-yl]methyl acetate
• CAS: 236755-48-9
• 化学式: C₂₂H₂₃N₅O₇
• 分子量: 469.454
• InChiKey: NQZKMHDVOAPKEP-OBZYLPMUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  34.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  157.75
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  (2R,3S,4S,5R)-2-(acetoxymethyl)-5-(2-amino-6-phenyl-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate 在 三溴甲烷 、 sodium methylate 、 nickel dibromide 、 亚硝酸异戊酯 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 8.0h， 生成 2-bromo-6-phenyl-9-(β-D-ribofuranosyl)purine
  参考文献：
  名称：

  Cytostatic 6-Arylpurine Nucleosides IV. Synthesis of 2-Substituted 6-Phenylpurine Ribonucleosides

  摘要：

  一系列2-X-取代-6-苯基-9-(β-D-核糖呋喃)嘌呤化合物(X = Cl, Br, I, CH₃, CF₃和Ph) 通过保护的2-氨基-6-苯基嘌呤核苷酸的卤代脱氨化反应、2,6-二卤代嘌呤与苯基硼酸的区域选择性Suzuki-Miyaura反应或相应的2-卤代-6-苯基嘌呤的交叉偶联反应后脱保护而制备。所有的核苷酸都没有表现出任何明显的细胞毒素活性。

  DOI：

  10.1135/cccc20020325
• 作为产物：
  描述：

  6-氯鸟嘌呤核苷 在 4-二甲氨基吡啶 、 四(三苯基膦)钯 、 potassium carbonate 、 三乙胺 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 27.0h， 生成 (2R,3S,4S,5R)-2-(acetoxymethyl)-5-(2-amino-6-phenyl-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate
  参考文献：
  名称：

  [RhCp*Cl₂]₂-Catalyzed Directed N-Boc Amidation of Arenes “on Water”

  摘要：

  Rhodium(III) catalysis on water is effective for directed C-H amidation of arenes. The catalytic process is promoted by OH groups present on the hydrophobic water surface and is inefficient in all (most) common organic solvents investigated so far. In the presence of easily prepared tert-butyl 2,4-dinitrophenoxycarbamate, a new and stable nitrene source, the on water reaction can efficiently provide the desired N-Boc-aminated products with good functional group tolerance.

  DOI：

  10.1021/acs.orglett.5b00392

文献信息

• Rhodium-Catalyzed Intermolecular Amidation of Arenes with Sulfonyl Azides via Chelation-Assisted C–H Bond Activation
  作者：Ji Young Kim、Sae Hume Park、Jaeyune Ryu、Seung Hwan Cho、Seok Hwan Kim、Sukbok Chang

  DOI：10.1021/ja303527m

  日期：2012.6.6

  We report the direct amidation of arene C-H bonds using sulfonyl azides as the amino source to release N(2) as the single byproduct. The reaction is catalyzed by a cationic rhodium complex under external oxidant-free conditions in the atmospheric environment. A broad range of chelate group-containing arenes are selectively amidated with excellent functional group tolerance, thus opening a new avenue

  我们报告使用磺酰叠氮化物作为氨基源释放 N(2) 作为单一副产品的芳烃 CH 键的直接酰胺化。该反应在大气环境中的外部无氧化剂条件下由阳离子铑络合物催化。广泛的含螯合基团的芳烃被选择性酰胺化，具有优异的官能团耐受性，从而为实际分子间 CN 键的形成开辟了新途径。
• Chelation-Assisted Rhodium-Catalyzed Direct Amidation with Amidobenziodoxolones: C(sp²)–H, C(sp³)–H, and Late-Stage Functionalizations
  作者：Xu-Hong Hu、Xiao-Fei Yang、Teck-Peng Loh

  DOI：10.1021/acscatal.6b02015

  日期：2016.9.2

  Air-stable and convenient amidobenziodoxolones as an amidating reagent were disclosed to enable direct amidation on a wide range of C(sp2)–H bonds of (hetero)arenes and alkenes, as well as unactivated C(sp3)–H bonds under RhIII catalysis. The approach to access 49 examples of structurally diverse amides is featured by mild conditions, complete chemoselectivity and regioselectivity, broad substrate scope

  公开了一种空气稳定且方便的酰胺基苯并恶唑烷酮作为酰胺化试剂，可以直接酰胺化广泛的（杂）芳烃和烯烃的C（sp 2）-H键，以及未活化的C（sp 3）-H键Rh III催化。获得49种结构多样的酰胺实例的方法的特点是温和条件，完全的化学选择性和区域选择性，广泛的底物范围（不限于强杂环配位基团）以及对有价值的功能性取代基（如未保护的胺和羟基）的耐受性。该协议的合成适用性也通过生物学上重要的支架的后期功能化得到证明。
• The Suzuki-Miyaura Cross-Coupling Reactions of 6-Halopurines with Boronic Acids Leading to 6-Aryl- and 6-Alkenylpurines
  作者：Martina Havelková、Michal Hocek、Michal Česnek、Dalimil Dvořák

  DOI：10.1055/s-1999-2753

  日期：1999.7
• Synthesis and Cytostatic Activity of Substituted 6-Phenylpurine Bases and Nucleosides:  Application of the Suzuki−Miyaura Cross-Coupling Reactions of 6-Chloropurine Derivatives with Phenylboronic Acids
  作者：Michal Hocek、Antonín Holý、Ivan Votruba、Hana Dvořáková

  DOI：10.1021/jm991167+

  日期：2000.5.1

  The Suzuki-Miyaura reaction of protected 6-chloropurine and 2-amino-6-chloropurine bases and nucleosides with substituted phenylboronic acids led to the corresponding protected 6-(substituted phenyl)purine derivatives 6-9. Their deprotection yielded a series of substituted 6-phenylpurine bases and nucleosides 10-13. Significant cytostatic activity (IC50 0.25-20 mu mol/L) in CCRF-CEM, HeLa, and L1210 cell lines was found for several 6-(4-X-substituted phenyl)purine ribonucleosides 12 (X = H, F, Cl, and OR), while the 6-phenylpurine and 2-amino-6-phenylpurine bases 10 and 11, as well as 2-amino-6-phenylpurine ribosides 13, were entirely inactive against these cell lines.