ethyl 2-[[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-3,4-bis(triethylsilyloxy)oxolan-2-yl]methylamino]acetate | 862490-60-6

• 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: ethyl 2-[[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-3,4-bis(triethylsilyloxy)oxolan-2-yl]methylamino]acetate
• CAS: 862490-60-6
• 化学式: C₂₆H₄₈N₆O₅Si₂
• 分子量: 580.875
• InChiKey: KWHOJFPLAVMHAE-VJUOEERUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.24
• 重原子数：
  39
• 可旋转键数：
  17
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  136
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  ethyl 2-[[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-3,4-bis(triethylsilyloxy)oxolan-2-yl]methylamino]acetate 在 咪唑 、 lithium aluminium tetrahydride 、 碘 、 重水 、 sodium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 5.5h， 生成 9-[(2R,3R,4S,5R)-5-(aziridin-1-ylmethyl)-3,4-dideuteriooxyoxolan-2-yl]-N,N-dideuteriopurin-6-amine
  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：

  2',3'-异丙叉腺苷 在 水 、 potassium carbonate 、 苯硫酚 、 三乙胺 、 三苯基膦 、 三氟乙酸 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 生成 ethyl 2-[[(2R,3R,4R,5R)-5-(6-aminopurin-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

文献信息

• <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.