2',3'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-N6-benzyladenosine | 862490-75-3

• 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: 2',3'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-N6-benzyladenosine
• CAS: 862490-75-3
• 化学式: C₂₉H₄₅N₅O₅Si₂
• 分子量: 599.878
• InChiKey: BKEDLUZQBGBOCT-CTDWIVFPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.65
• 重原子数：
  41.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  112.78
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  2',3'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-N6-benzyladenosine 在 potassium carbonate 、 苯硫酚 、 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 为溶剂， 反应 14.5h， 生成 {[(1R,3R,3aR,8aR)-3-(6-Benzylamino-purin-9-yl)-5,5,7,7-tetraisopropyl-tetrahydro-2,4,6,8-tetraoxa-5,7-disila-azulen-1-ylmethyl]-amino}-acetic acid ethyl ester
  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-苄基腺苷 在 吡啶 、 甲烷磺酸 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.17h， 生成 2',3'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-N6-benzyladenosine
  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