cis-4(R)-(6-chloro-9H-purin-9-yl)-1(S)-N-[N-tert-butyloxycarbonyl(benzyloxy)amino]-cyclopent-2-ene | 210162-79-1

• 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-chloro-9H-purin-9-yl)-1(S)-N-[N-tert-butyloxycarbonyl(benzyloxy)amino]-cyclopent-2-ene
• 英文别名: tert-butyl N-[(1S,4R)-4-(6-chloropurin-9-yl)cyclopent-2-en-1-yl]-N-phenylmethoxycarbamate
• CAS: 210162-79-1
• 化学式: C₂₂H₂₄ClN₅O₃
• 分子量: 441.917
• InChiKey: ZYYRFNDRXDBGTL-DLBZAZTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.72
• 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：
  82.37
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  cis-4(R)-(6-chloro-9H-purin-9-yl)-1(S)-N-[N-tert-butyloxycarbonyl(benzyloxy)amino]-cyclopent-2-ene 在 ruthenium trichloride 、 sodium periodate 、 对甲苯磺酸 作用下， 以 水 、 乙酸乙酯 、 丙酮 、 乙腈 为溶剂， 反应 15.04h， 生成 5(R)-(6-chloro-9H-purin-9-yl)-3(S)-N-[N-tert-butyloxycarbonyl(benzyloxy)amino]-1(S),2(R)-(isopropylidenedioxy)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 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 17.5h， 生成 cis-4(R)-(6-chloro-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