9-(3-O-benzoyl-2-O-benzyl-β-D-ribofuranosyl)-6-chloropurine | 568584-95-2

• 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: 9-(3-O-benzoyl-2-O-benzyl-β-D-ribofuranosyl)-6-chloropurine
• 英文别名: [(2R,3R,4R,5R)-5-(6-chloropurin-9-yl)-2-(hydroxymethyl)-4-phenylmethoxyoxolan-3-yl] benzoate
• CAS: 568584-95-2
• 化学式: C₂₄H₂₁ClN₄O₅
• 分子量: 480.908
• InChiKey: LQJMESQTJYKNBP-ZDXOVATRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  9-(3-O-benzoyl-2-O-benzyl-β-D-ribofuranosyl)-6-chloropurine 在 palladium on activated charcoal 氨 、 氢气 作用下， 以 甲醇 、 乙醇 为溶剂， 生成 腺苷
  参考文献：
  名称：

  A New Method for the Synthesis of 2′-O-Benzyladenosine Using Mitsunobu Reaction

  摘要：

  A new method to introduce a benzyl group onto the 2'-OH of purine ribonucleoside is described. Thus, 6-chloropurine 3'-O-benzoylriboside and its 5'-O-trityl congener were condensed with benzyl alcohol using the Mitsunobu reaction to give the 2'-O-benzyl derivative. The yields were varied from 4.6 to 62.9% depending on the solvent used. The product was converted to adenosine, indicating that the stereochemistry at C-2' is retained.

  DOI：

  10.1081/ncn-120019506
• 作为产物：
  描述：

  6-chloro-9-(3-O-benzoyl-β-D-ribofuranosyl)purine 、 苯甲醇 在 偶氮二甲酰胺 、 三苯基膦 作用下， 生成 9-(3-O-benzoyl-2-O-benzyl-β-D-ribofuranosyl)-6-chloropurine
  参考文献：
  名称：

  Introduction of a Benzyl Group onto the 2′-OH of 6-Chloropurine 3′-O-Benzoylriboside

  摘要：

  A new method to introduce a benzyl group onto the 2'-OH of purine ribonucleoside is described. Thus, 6-chloropurine 3'-O-benzoylriboside and its 5'-O-trityl congener were condensed with benzyl alcohol using the Mitsunobu reaction to give the 2'-O-benzyl derivative. The yields were varied from 4.6 to 62.9%, depending on the solvent. The product was converted to adenosine, indicating that the stereochemistry at C-2' is retained.

  DOI：

  10.1081/ncn-120022633

文献信息

• A New Method for the Synthesis of 2′-<i>O</i>-Benzyladenosine Using Mitsunobu Reaction
  作者：Shigetada Kozai、Tomoyo Fuzikawa、Keisuke Harumoto、Tokumi Maruyama

  DOI：10.1081/ncn-120019506

  日期：2003.5

  A new method to introduce a benzyl group onto the 2'-OH of purine ribonucleoside is described. Thus, 6-chloropurine 3'-O-benzoylriboside and its 5'-O-trityl congener were condensed with benzyl alcohol using the Mitsunobu reaction to give the 2'-O-benzyl derivative. The yields were varied from 4.6 to 62.9% depending on the solvent used. The product was converted to adenosine, indicating that the stereochemistry at C-2' is retained.
• Introduction of a Benzyl Group onto the 2′-OH of 6-Chloropurine 3′-<i>O</i>-Benzoylriboside
  作者：Shigetada Kozai、Tomoyo Fuzikawa、Keisuke Harumoto、Tokumi Maruyama

  DOI：10.1081/ncn-120022633

  日期：2003.10

  A new method to introduce a benzyl group onto the 2'-OH of purine ribonucleoside is described. Thus, 6-chloropurine 3'-O-benzoylriboside and its 5'-O-trityl congener were condensed with benzyl alcohol using the Mitsunobu reaction to give the 2'-O-benzyl derivative. The yields were varied from 4.6 to 62.9%, depending on the solvent. The product was converted to adenosine, indicating that the stereochemistry at C-2' is retained.