[(3aR,4R,6R,6aR)-6-(6-aminopurin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-ylmethyl]-(2-chloroethyl)carbamic acid 4,5-dimethoxy-2-nitrobenzyl ester | 1172048-20-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [(3aR,4R,6R,6aR)-6-(6-aminopurin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-ylmethyl]-(2-chloroethyl)carbamic acid 4,5-dimethoxy-2-nitrobenzyl ester
• 英文别名: (4,5-dimethoxy-2-nitrophenyl)methyl N-[[(3aR,4R,6R,6aR)-4-(6-aminopurin-9-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methyl]-N-(2-chloroethyl)carbamate
• CAS: 1172048-20-2
• 化学式: C₂₅H₃₀ClN₇O₉
• 分子量: 608.008
• InChiKey: HVJFBPMHIYPRBL-ZDXOVATRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  42
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  191
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  [(3aR,4R,6R,6aR)-6-(6-aminopurin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-ylmethyl]-(2-chloroethyl)carbamic acid 4,5-dimethoxy-2-nitrobenzyl ester 在 水 、 三氟乙酸 作用下， 以78%的产率得到[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxytetrahydrofuran-2-ylmethyl](2-chloroethyl)carbamic acid 4,5-dimethoxy-2-nitrobenzyl ester
  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：

  [(3aR,4R,6R,6aR)-6-(6-aminopurin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-ylmethyl]-(2-hydroxyethyl)carbamic acid 4,5-dimethoxy-2-nitrobenzyl ester 在 四氯化碳 、 三苯基膦 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以94%的产率得到[(3aR,4R,6R,6aR)-6-(6-aminopurin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-ylmethyl]-(2-chloroethyl)carbamic acid 4,5-dimethoxy-2-nitrobenzyl ester
  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.