O-Benzyl-N-[(1S,4R)-4-(6-chloro-purin-9-yl)-cyclopent-2-enyl]-hydroxylamine | 210162-83-7

• 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: O-Benzyl-N-[(1S,4R)-4-(6-chloro-purin-9-yl)-cyclopent-2-enyl]-hydroxylamine
• 英文别名: (1S,4R)-4-(6-chloropurin-9-yl)-N-phenylmethoxycyclopent-2-en-1-amine
• CAS: 210162-83-7
• 化学式: C₁₇H₁₆ClN₅O
• 分子量: 341.8
• InChiKey: BQWYVBVGGCBESH-KGLIPLIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.07
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  64.86
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  O-Benzyl-N-[(1S,4R)-4-(6-chloro-purin-9-yl)-cyclopent-2-enyl]-hydroxylamine 在 吡啶 、 4-二甲氨基吡啶 、 氨 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 36.0h， 生成 N-[(1S,4R)-4-(6-Amino-purin-9-yl)-cyclopent-2-enyl]-N-benzyloxy-acetamide
  参考文献：
  名称：

  Syntheses of novel hydroxylamine carbanucleosides

  摘要：

  Enantiomerically pure 4'-hydroxylamino-adenine-derived carbanucleosides have been synthesized as isosteric 4'-hydroxymethyl analogs to carbovir, ddA, and aristeromycin. The key steps in the syntheses involved an enzymatic desymmetrization, two subsequent Mitsunobu reactions, and a highly diastereoselective ruthenium tetroxide-mediated dihydroxylation, overcoming the syn-directing effect seen in osmium tetroxide-mediated dihydroxylations. Hydroxylamino-propane analogs were also synthesized through similar methodology to afford adenine and cyclopropylamino purine analogs to acyclovir. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00359-7
• 作为产物：
  描述：

  (1R,4R)-4-(6-chloro-9H-purin-9-yl)cyclopent-2-en-1-yl acetate 在 potassium cyanide 、 偶氮二甲酸二苄酯 、 三苯基膦 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 18.25h， 生成 O-Benzyl-N-[(1S,4R)-4-(6-chloro-purin-9-yl)-cyclopent-2-enyl]-hydroxylamine
  参考文献：
  名称：

  Syntheses of novel hydroxylamine carbanucleosides

  摘要：

  Enantiomerically pure 4'-hydroxylamino-adenine-derived carbanucleosides have been synthesized as isosteric 4'-hydroxymethyl analogs to carbovir, ddA, and aristeromycin. The key steps in the syntheses involved an enzymatic desymmetrization, two subsequent Mitsunobu reactions, and a highly diastereoselective ruthenium tetroxide-mediated dihydroxylation, overcoming the syn-directing effect seen in osmium tetroxide-mediated dihydroxylations. Hydroxylamino-propane analogs were also synthesized through similar methodology to afford adenine and cyclopropylamino purine analogs to acyclovir. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00359-7