(2R,4R,5R)-2-(6-amino-9H-purin-9-yl)-4-((tert-butyldimethylsilyl)oxy)-5-(((tert-butyldimethylsilyl)oxy)methyl)dihydrofuran-3,3(2H)-diol | 129835-14-9

• 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,4R,5R)-2-(6-amino-9H-purin-9-yl)-4-((tert-butyldimethylsilyl)oxy)-5-(((tert-butyldimethylsilyl)oxy)methyl)dihydrofuran-3,3(2H)-diol
• 英文别名: (2R,4R,5R)-2-(6-aminopurin-9-yl)-4-[tert-butyl(dimethyl)silyl]oxy-5-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolane-3,3-diol
• CAS: 129835-14-9
• 化学式: C₂₂H₄₁N₅O₅Si₂
• 分子量: 511.769
• InChiKey: PYMCMICBBVBXRR-IDHHARJASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  34.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  137.77
• 氢给体数：
  3.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (2R,4R,5R)-2-(6-amino-9H-purin-9-yl)-4-((tert-butyldimethylsilyl)oxy)-5-(((tert-butyldimethylsilyl)oxy)methyl)dihydrofuran-3,3(2H)-diol 在 sodium tetrahydroborate 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以87%的产率得到9-<3,5-bis-O-(tert-butyldimethylsilyl)-β-D-arabinofuranosyl>adenine
  参考文献：
  名称：

  Synthesis of non-hydrolyzable substrate analogs for Asp-tRNAAsn/Glu-tRNAGln amidotransferase

  摘要：

  Non-hydrolyzable substrate analogs for tRNA-dependent amidotransferase, 2'- or 3'-aspartyl or -glutamyl adenosine, were synthesized from adenosine without protection of the adenine base. The hydroxyl groups of adenosine were selectively protected, followed by a series of oxidation/reductions to alter the stereochemistry. DFT calculations revealed the driving forces for the ketone hydrate formation at C-2', but not the C-3' carbon during the oxidation step. Subsequently, triflation and azide replacement yielded azidoadenosines, which were coupled to protected amino acids after deprotection and reduction. After global deprotection, the target substrate analogs were obtained in 2-14% overall yields from adenosine. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.09.060
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 在 吡啶 、 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 96.0h， 生成 (2R,4R,5R)-2-(6-amino-9H-purin-9-yl)-4-((tert-butyldimethylsilyl)oxy)-5-(((tert-butyldimethylsilyl)oxy)methyl)dihydrofuran-3,3(2H)-diol
  参考文献：
  名称：

  Synthesis of non-hydrolyzable substrate analogs for Asp-tRNAAsn/Glu-tRNAGln amidotransferase

  摘要：

  Non-hydrolyzable substrate analogs for tRNA-dependent amidotransferase, 2'- or 3'-aspartyl or -glutamyl adenosine, were synthesized from adenosine without protection of the adenine base. The hydroxyl groups of adenosine were selectively protected, followed by a series of oxidation/reductions to alter the stereochemistry. DFT calculations revealed the driving forces for the ketone hydrate formation at C-2', but not the C-3' carbon during the oxidation step. Subsequently, triflation and azide replacement yielded azidoadenosines, which were coupled to protected amino acids after deprotection and reduction. After global deprotection, the target substrate analogs were obtained in 2-14% overall yields from adenosine. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.09.060

文献信息

• Nucleic acid related compounds. 60. Mild periodinane oxidation of protected nucleosides to give 2'- and 3'-ketonucleosides. The first isolation of a purine 2'-deoxy-3'-ketonucleoside derivative
  作者：Vicente Samano、Morris J. Robins

  DOI：10.1021/jo00305a003

  日期：1990.8
• SAMANO, VICENTE;ROBINS, MORRIS J., J. ORG. CHEM., 55,(1990) N8, C. 5186-5188
  作者：SAMANO, VICENTE、ROBINS, MORRIS J.

  DOI：——

  日期：——