(S)-3-[9-(2-deoxy-β-D-erythro-pentofuranosyl)purin-6-yl]-2-[(benzyloxycarbonyl)amino]propanoic acid | 807626-45-5

• 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: (S)-3-[9-(2-deoxy-β-D-erythro-pentofuranosyl)purin-6-yl]-2-[(benzyloxycarbonyl)amino]propanoic acid
• 英文别名: (2S)-3-[9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-6-yl]-2-(phenylmethoxycarbonylamino)propanoic acid
• CAS: 807626-45-5
• 化学式: C₂₁H₂₃N₅O₇
• 分子量: 457.443
• InChiKey: KOAGQBWSFCSIPA-MWDXBVQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  169
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (S)-3-[9-(2-deoxy-β-D-erythro-pentofuranosyl)purin-6-yl]-2-[(benzyloxycarbonyl)amino]propanoic acid 在 palladium on activated charcoal 氢气 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 16.0h， 以70%的产率得到(S)-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：

  6-碘嘌呤 在 sodium hydroxide 、 三甲基氯硅烷 、 sodium hydride 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 19.34h， 生成 (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

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.