6-chloropurine 2',3'-di-O-benzoylriboside | 228243-46-7

• 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: 6-chloropurine 2',3'-di-O-benzoylriboside
• 英文别名: C6-chloro-2',3'-bis(O-benzoyl)adenosine；[(2R,3R,4R,5R)-4-benzoyloxy-5-(6-chloropurin-9-yl)-2-(hydroxymethyl)oxolan-3-yl] benzoate
• CAS: 228243-46-7
• 化学式: C₂₄H₁₉ClN₄O₆
• 分子量: 494.891
• InChiKey: GBFYOWPOSQUHID-WGQQHEPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  126
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  6-chloropurine 2',3'-di-O-benzoylriboside 在 咪唑 、 甲醇 、 lithium aluminium tetrahydride 、 sodium methylate 、 potassium carbonate 、 苯硫酚 、 N,N-二异丙基乙胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 50.75h， 生成 2-[[(2R,3R,4R,5R)-5-[6-(benzylamino)purin-9-yl]-3,4-bis(triethylsilyloxy)oxolan-2-yl]methylamino]ethanol
  参考文献：
  名称：

  o-Nitrobenzenesulfonamides in Nucleoside Synthesis:  Efficient 5‘-Aziridination of Adenosine

  摘要：

  5'-Aziridinoadenylates of the form 1 and a related nitrogen mustard variant have been constructed using a novel variation of the Mitsunobu reaction. Such molecules allow conversion of biological methyltransferases into nucleoside transferases, thus providing powerful tools for investigating S-adenosyl-L-methionine (SAM)-dependent methylation. We present here a highly effective synthesis of such molecules that is amenable to aziridine diversification as well as elaboration of the base moiety so as to afford "bumped" cofactor mimics compatible with "hole"-bearing mutant proteins.

  DOI：

  10.1021/jo050205w
• 作为产物：
  描述：

  6-氯嘌呤核苷 、 苯甲酰氯 在 sodium carbonate 作用下， 以 水 、 乙腈 为溶剂， 反应 0.58h， 以93%的产率得到6-chloropurine 2',3'-di-O-benzoylriboside
  参考文献：
  名称：

  o-Nitrobenzenesulfonamides in Nucleoside Synthesis:  Efficient 5‘-Aziridination of Adenosine

  摘要：

  5'-Aziridinoadenylates of the form 1 and a related nitrogen mustard variant have been constructed using a novel variation of the Mitsunobu reaction. Such molecules allow conversion of biological methyltransferases into nucleoside transferases, thus providing powerful tools for investigating S-adenosyl-L-methionine (SAM)-dependent methylation. We present here a highly effective synthesis of such molecules that is amenable to aziridine diversification as well as elaboration of the base moiety so as to afford "bumped" cofactor mimics compatible with "hole"-bearing mutant proteins.

  DOI：

  10.1021/jo050205w

文献信息

• Introduction of a benzoyl group onto riboside in aqueous solution: One-step synthesis of 6-chloropurine 2′,3′-di-O-benzoylriboside
  作者：Shigetada Kozai、Satoshi Takamatsu、Kunisuke Izawa、Tokumi Maruyama

  DOI：10.1016/s0040-4039(99)00747-9

  日期：1999.6

  A benzoyl group was introduced onto the 3'-hydroxyl group of 6-chloropurine riboside by treatment with benzoylating agents in the presence of an organic or inorganic base in aqueous solution, in which further reaction gave 6-chloropurine 2',3'-di-O-benzoylriboside. (C) 1999 Elsevier Science Ltd. Ali rights reserved.
• <i>o</i>-Nitrobenzenesulfonamides in Nucleoside Synthesis:  Efficient 5‘-Aziridination of Adenosine
  作者：Scott G. Petersen、Scott R. Rajski

  DOI：10.1021/jo050205w

  日期：2005.7.1

  5'-Aziridinoadenylates of the form 1 and a related nitrogen mustard variant have been constructed using a novel variation of the Mitsunobu reaction. Such molecules allow conversion of biological methyltransferases into nucleoside transferases, thus providing powerful tools for investigating S-adenosyl-L-methionine (SAM)-dependent methylation. We present here a highly effective synthesis of such molecules that is amenable to aziridine diversification as well as elaboration of the base moiety so as to afford "bumped" cofactor mimics compatible with "hole"-bearing mutant proteins.