benzyl (S)-3-[9-(3,5-di-O-p-toluoyl-2-deoxy-β-D-erythro-pentofuranosyl)purin-6-yl]-2-[(benzyloxycarbonyl)amino]propanoate | 807626-41-1

• 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 (S)-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: [(2R,3S,5R)-3-(4-methylbenzoyl)oxy-5-[6-[(2S)-3-oxo-3-phenylmethoxy-2-(phenylmethoxycarbonylamino)propyl]purin-9-yl]oxolan-2-yl]methyl 4-methylbenzoate
• CAS: 807626-41-1
• 化学式: C₄₄H₄₁N₅O₉
• 分子量: 783.838
• InChiKey: TYAMNTUQYFWBKG-CDBYGCFJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  58
• 可旋转键数：
  18
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  170
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  benzyl (S)-3-[9-(3,5-di-O-p-toluoyl-2-deoxy-β-D-erythro-pentofuranosyl)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 0.67h， 以95%的产率得到(S)-3-[9-(2-deoxy-β-D-erythro-pentofuranosyl)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：

  6-碘嘌呤 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 (S)-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

文献信息

• A Facile and Efficient Synthesis of (Purin-6-yl)alanines
  作者：Petr Čapek、Radek Pohl、Michal Hocek

  DOI：10.1021/jo048812r

  日期：2004.11.1

  (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.