3'-azido-6-N-[(di-n-butylamino)methylene]-2',5'-bis-O-(tert-butyldimethylsilyl)-3'-deoxy-β-D-adenosine

• 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: 3'-azido-6-N-[(di-n-butylamino)methylene]-2',5'-bis-O-(tert-butyldimethylsilyl)-3'-deoxy-β-D-adenosine
• 英文别名: N'-[9-[(2R,3R,4R,5S)-4-azido-3-[tert-butyl(dimethyl)silyl]oxy-5-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-2-yl]purin-6-yl]-N,N-dibutylmethanimidamide
• 化学式: C₃₁H₅₇N₉O₃Si₂
• 分子量: 660.023
• InChiKey: LRFAJWBJZMWIDO-SEUURLFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.38
• 重原子数：
  45
• 可旋转键数：
  17
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  101
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3'-azido-6-N-[(di-n-butylamino)methylene]-2',5'-bis-O-(tert-butyldimethylsilyl)-3'-deoxy-β-D-adenosine 在 甲胺 作用下， 以 乙醇 为溶剂， 反应 8.0h， 生成 3'-azido-2',5'-bis-O-(tert-butyldimethylsilyl)-3'-deoxyadenosine
  参考文献：
  名称：

  Facile and Rapid Access to Inosine Puromycin Analogues through the Use of Adenylate Deaminase

  摘要：

  To study the ribosomal peptidyl transfer, puromycin analogues are of interest in which adenine has been replaced by hypoxanthine. We synthesized inosine puromycin analogues from 3'-azidodeoxyadenosine derivatives using adenylate deaminase for the quantitative transformation of the N-heterocycle. The amino acid coupling was carried out under Staudinger-Vilarrasa conditions in 94% yield starting from the protected and in 82% using the unprotected azide, thus, in the presence of two hydroxyls and a lactam function.

  DOI：

  10.1021/ol070818q
• 作为产物：
  描述：

  9-(2,5-di-O-tert-butyldimethylsilyl-β-D-erythro-pentofuran-3-ulosyl)adenosine 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 叠氮化锂 作用下， 以 甲醇 、 二氯甲烷 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 62.5h， 生成 3'-azido-6-N-[(di-n-butylamino)methylene]-2',5'-bis-O-(tert-butyldimethylsilyl)-3'-deoxy-β-D-adenosine
  参考文献：
  名称：

  3'-氨基-3'-脱氧腺苷衍生物和嘌呤霉素类似物的实用途径。

  摘要：

  3'-氨基酰基氨基-3'-脱氧腺苷是抗生素嘌呤霉素的类似物，是由腺苷合成的。它们的关键3'-叠氮基衍生物10是通过3'-氧化/还原/取代过程获得的。使用Garegg试剂为氧化步骤开发了大规模的改良纯化方案。Fmoc-1-氨基酸与3'-氨基-3'-脱氧腺苷11的完全保护形式之间的偶联反应以高收率提供了氨基酰化的化合物12。嘌呤霉素类似物以10个步骤获得，总产率高达23％（14c）。

  DOI：

  10.1021/jo026627c

文献信息

• Shorter puromycin analog synthesis by means of an efficient Staudinger–Vilarrasa coupling
  作者：Hubert Chapuis、Peter Strazewski

  DOI：10.1016/j.tet.2006.09.045

  日期：2006.12

  An efficient Staudinger–Vilarrasa coupling generates amides from azides and 1-hydroxybenzotriazole esters of amino- or hydroxy acid derivatives in very high isolated yields and purity. New puromycin analogs, mostly putative biosynthetic intermediates, were synthesized in nine steps from adenosine.

  有效的Staudinger-Vilarrasa偶联可从叠氮化物和氨基或羟基酸衍生物的1-羟基苯并三唑酯生成酰胺，分离产率和纯度很高。新的嘌呤霉素类似物（主要是假定的生物合成中间体）是从腺苷经九步合成的。
• Synthesis of an Alanyl Adenosine Analog
  作者：Oliver Botta、Peter Strazewski

  DOI：10.1080/15257779908041553

  日期：1999.4

  The synthetic route towards a 3'-alanyl-3'-amino-3'-deoxyadenosine derivative is described which allows the automated synthesis of 3'-aminoacylated RNA strands.
• A Practical Route to 3‘-Amino-3‘-deoxyadenosine Derivatives and Puromycin Analogues
  作者：Nhat Quang Nguyen-Trung、Oliver Botta、Silvia Terenzi、Peter Strazewski

  DOI：10.1021/jo026627c

  日期：2003.3.1

  3'-aminoacylamino-3'-deoxyadenosines, analogues of the antibiotic puromycin, have been synthesized from adenosine. They key 3'-azido derivative 10 was obtained through a 3'-oxidation/reduction/substitution procedure. A modified purification protocol on a larger scale was developed for the oxidation step using the Garegg reagent. The coupling reaction between an Fmoc-l-amino acid and the fully protected

  3'-氨基酰基氨基-3'-脱氧腺苷是抗生素嘌呤霉素的类似物，是由腺苷合成的。它们的关键3'-叠氮基衍生物10是通过3'-氧化/还原/取代过程获得的。使用Garegg试剂为氧化步骤开发了大规模的改良纯化方案。Fmoc-1-氨基酸与3'-氨基-3'-脱氧腺苷11的完全保护形式之间的偶联反应以高收率提供了氨基酰化的化合物12。嘌呤霉素类似物以10个步骤获得，总产率高达23％（14c）。
• Facile and Rapid Access to Inosine Puromycin Analogues through the Use of Adenylate Deaminase
  作者：Adib Charafeddine、Hubert Chapuis、Peter Strazewski

  DOI：10.1021/ol070818q

  日期：2007.7.1

  To study the ribosomal peptidyl transfer, puromycin analogues are of interest in which adenine has been replaced by hypoxanthine. We synthesized inosine puromycin analogues from 3'-azidodeoxyadenosine derivatives using adenylate deaminase for the quantitative transformation of the N-heterocycle. The amino acid coupling was carried out under Staudinger-Vilarrasa conditions in 94% yield starting from the protected and in 82% using the unprotected azide, thus, in the presence of two hydroxyls and a lactam function.