benzyl 3-[9-(3,5-di-O-p-toluoyl-2-deoxy-β-D-erythro-pentofuranosyl)purin-6-yl]-2-[(benzyloxycarbonyl)amino]propanoate | 787550-85-0

• 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: benzyl 3-[9-(3,5-di-O-p-toluoyl-2-deoxy-β-D-erythro-pentofuranosyl)purin-6-yl]-2-[(benzyloxycarbonyl)amino]propanoate
• 英文别名: benzyl (R,S)-3-[9-(3,5-di-o-para-toluyl-β-D-2'-deoxyribofuranosyl)purin-6-yl]-2-[(benzyloxycarbonyl)amino]propanoate
• CAS: 787550-85-0
• 化学式: C₄₄H₄₁N₅O₉
• 分子量: 783.838
• InChiKey: TYAMNTUQYFWBKG-OUSJJARPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.39
• 重原子数：
  58.0
• 可旋转键数：
  14.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  170.06
• 氢给体数：
  1.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  benzyl 3-[9-(3,5-di-O-p-toluoyl-2-deoxy-β-D-erythro-pentofuranosyl)purin-6-yl]-2-[(benzyloxycarbonyl)amino]propanoate 在 palladium on activated charcoal sodium hydroxide 、 氢气 、 溶剂黄146 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 水 为溶剂， 反应 16.67h， 生成 3-[9-(2-deoxy-β-D-erythro-pentofuranosyl)purin-6-yl]-2-aminopropanoic acid
  参考文献：
  名称：

  A Facile and Efficient Synthesis of (Purin-6-yl)alanines

  摘要：

  (Purin-6-yl)alanines, a new class of amino acid-nucleobase conjugates, were synthesized by palladium-catalyzed cross-coupling reactions of protected iodozincalanines with 6-iodopurines (9-Bn-6-iodopurine and 9-THP-6-iodopurine as well as acyl-protected 6-iodopurine ribonucleoside and 2-deoxyribonucleoside). Free purine base and nucleosides bearing alanine in position 6 were obtained after complete deprotection of the products of cross-coupling reactions.

  DOI：

  10.1021/jo048812r
• 作为产物：
  描述：

  2-deoxy-3,5-di-O-(p-toluoyl)-α-D-erythropentofuranosyl chloride 在 三甲基氯硅烷 、 sodium hydride 、 锌 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 18.67h， 生成 benzyl 3-[9-(3,5-di-O-p-toluoyl-2-deoxy-β-D-erythro-pentofuranosyl)purin-6-yl]-2-[(benzyloxycarbonyl)amino]propanoate
  参考文献：
  名称：

  A Facile and Efficient Synthesis of (Purin-6-yl)alanines

  摘要：

  (Purin-6-yl)alanines, a new class of amino acid-nucleobase conjugates, were synthesized by palladium-catalyzed cross-coupling reactions of protected iodozincalanines with 6-iodopurines (9-Bn-6-iodopurine and 9-THP-6-iodopurine as well as acyl-protected 6-iodopurine ribonucleoside and 2-deoxyribonucleoside). Free purine base and nucleosides bearing alanine in position 6 were obtained after complete deprotection of the products of cross-coupling reactions.

  DOI：

  10.1021/jo048812r