cis-4(R)-(6-amino-9H-purin-9-yl)-1(S)-N-[N-tert-butyloxycarbonyl(benzyloxy)amino]cyclopent-2-ene | 210162-80-4

• 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: cis-4(R)-(6-amino-9H-purin-9-yl)-1(S)-N-[N-tert-butyloxycarbonyl(benzyloxy)amino]cyclopent-2-ene
• CAS: 210162-80-4
• 化学式: C₂₂H₂₆N₆O₃
• 分子量: 422.487
• InChiKey: KDSUQMSLPIMQPO-DLBZAZTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.65
• 重原子数：
  31.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  108.39
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  cis-4(R)-(6-amino-9H-purin-9-yl)-1(S)-N-[N-tert-butyloxycarbonyl(benzyloxy)amino]cyclopent-2-ene 在 palladium dihydroxide 、 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 60.0h， 以80%的产率得到cis-3(S)-(6-amino-9H-purin-9-yl)-1(R)-N-(N-tert-butyloxycarbonylhydroxamino)cyclopentane
  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 、 氨 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 41.5h， 生成 cis-4(R)-(6-amino-9H-purin-9-yl)-1(S)-N-[N-tert-butyloxycarbonyl(benzyloxy)amino]cyclopent-2-ene
  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