9-{(3aR,4R,6R,6aR)-6-[(2-chloroethylamino)methyl]-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl}-9H-purin-6-ylamine | 1172048-09-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 9-{(3aR,4R,6R,6aR)-6-[(2-chloroethylamino)methyl]-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl}-9H-purin-6-ylamine
• 英文别名: 5'-(2-chloroethyl)amino-5'-deoxy-2',3'-O-isopropylideneadenosine；9-[(3aR,4R,6R,6aR)-6-[(2-chloroethylamino)methyl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]purin-6-amine
• CAS: 1172048-09-7
• 化学式: C₁₅H₂₁ClN₆O₃
• 分子量: 368.823
• InChiKey: XHORUYQZKDQTCB-IDTAVKCVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  109
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  9-{(3aR,4R,6R,6aR)-6-[(2-chloroethylamino)methyl]-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl}-9H-purin-6-ylamine 在 水 、 三氟乙酸 作用下， 反应 3.0h， 生成 (2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-[(2-chloroethylamino)methyl]tetrahydrofuran-3,4-diol
  参考文献：
  名称：

  New S-Adenosyl-l-methionine Analogues: Synthesis and Reactivity Studies

  摘要：

  Two new and complementary synthetic strategies for 5'-N-chloroethylamino-5'-deoxyadenosines are presented. Additionally, the reaction kinetics of their conversion into aziridines under typical enzyme assay conditions is reported using time-resolved NMR spectroscopy. A stable photocaged derivative of 5'-N-chloroethylamino-5'-deoxyadenosine has also been synthesized, and its stability and activation In aqueous solution at physiological pH have been examined.

  DOI：

  10.1021/ol9009859
• 作为产物：
  描述：

  氯乙醛 、 5-氨基-5-脱氧-2,3-O-(1-甲基亚乙基)-腺苷酸 在 盐酸 、 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 反应 120.0h， 生成 9-{(3aR,4R,6R,6aR)-6-[(2-chloroethylamino)methyl]-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl}-9H-purin-6-ylamine
  参考文献：
  名称：

  New S-Adenosyl-l-methionine Analogues: Synthesis and Reactivity Studies

  摘要：

  Two new and complementary synthetic strategies for 5'-N-chloroethylamino-5'-deoxyadenosines are presented. Additionally, the reaction kinetics of their conversion into aziridines under typical enzyme assay conditions is reported using time-resolved NMR spectroscopy. A stable photocaged derivative of 5'-N-chloroethylamino-5'-deoxyadenosine has also been synthesized, and its stability and activation In aqueous solution at physiological pH have been examined.

  DOI：

  10.1021/ol9009859

文献信息

• New <i>S</i>-Adenosyl-<scp>l</scp>-methionine Analogues: Synthesis and Reactivity Studies
  作者：Andrew P. Townsend、Stefanie Roth、Huw E. L. Williams、Eleni Stylianou、Neil R. Thomas

  DOI：10.1021/ol9009859

  日期：2009.7.16

  Two new and complementary synthetic strategies for 5'-N-chloroethylamino-5'-deoxyadenosines are presented. Additionally, the reaction kinetics of their conversion into aziridines under typical enzyme assay conditions is reported using time-resolved NMR spectroscopy. A stable photocaged derivative of 5'-N-chloroethylamino-5'-deoxyadenosine has also been synthesized, and its stability and activation In aqueous solution at physiological pH have been examined.