benzyl 3-[9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purin-6-yl]-2-[(benzyloxycarbonyl)amino]propanoate | 787550-84-9

• 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: benzyl 3-[9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purin-6-yl]-2-[(benzyloxycarbonyl)amino]propanoate
• 英文别名: benzyl (R,S)-3-[9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purin-6-yl]-2-[(benzyloxycarbonyl)amino]propanoate
• CAS: 787550-84-9
• 化学式: C₃₄H₃₅N₅O₁₁
• 分子量: 689.679
• InChiKey: SFHXSDVCCDIIQX-FYWSLROVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.73
• 重原子数：
  50.0
• 可旋转键数：
  13.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  196.36
• 氢给体数：
  1.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  benzyl 3-[9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purin-6-yl]-2-[(benzyloxycarbonyl)amino]propanoate 在 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 0.42h， 以97%的产率得到3-[9-(β-D-ribofuranosyl)purin-6-yl]-2-[(benzyloxycarbonyl)amino]propanoic 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-Benzyloxycarbonylamino-3-iodo-propionic acid benzyl ester 、 6-iodo-9-[β-(2',3',5'-tri-O-acetyl)-D-ribofuranosyl]purine 在 tris-(dibenzylideneacetone)dipalladium(0) 、 三(邻甲基苯基)磷 三甲基氯硅烷 、 锌 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.67h， 以80%的产率得到benzyl 3-[9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)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