[(2R,3R,4R,5R)-4-benzoyloxy-5-(6-chloropurin-9-yl)-2-[[(2-ethoxy-2-oxoethyl)-(2-nitrophenyl)sulfonylamino]methyl]oxolan-3-yl] benzoate | 862490-66-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 5'-脱氧核糖核苷
• 英文名称: [(2R,3R,4R,5R)-4-benzoyloxy-5-(6-chloropurin-9-yl)-2-[[(2-ethoxy-2-oxoethyl)-(2-nitrophenyl)sulfonylamino]methyl]oxolan-3-yl] benzoate
• CAS: 862490-66-2
• 化学式: C₃₄H₂₉ClN₆O₁₁S
• 分子量: 765.157
• InChiKey: AKFBZPHTPFLUHG-ZLSXUHLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  53
• 可旋转键数：
  15
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  223
• 氢给体数：
  0
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4R,5R)-4-benzoyloxy-5-(6-chloropurin-9-yl)-2-[[(2-ethoxy-2-oxoethyl)-(2-nitrophenyl)sulfonylamino]methyl]oxolan-3-yl] benzoate 在 咪唑 、 甲醇 、 sodium methylate 、 potassium carbonate 、 苯硫酚 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 43.0h， 生成 ethyl 2-[[(2R,3R,4R,5R)-5-[6-(benzylamino)purin-9-yl]-3,4-bis(triethylsilyloxy)oxolan-2-yl]methylamino]acetate
  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 在 sodium carbonate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 5.58h， 生成 [(2R,3R,4R,5R)-4-benzoyloxy-5-(6-chloropurin-9-yl)-2-[[(2-ethoxy-2-oxoethyl)-(2-nitrophenyl)sulfonylamino]methyl]oxolan-3-yl] benzoate
  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