5(R)-(6-chloro-9H-purin-9-yl)-1(S),2(R)-dihydroxy-3(S)-N-[N-tert-butyloxycarbonyl(benzyloxy)amino]cyclopentane | 210162-87-1

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 5(R)-(6-chloro-9H-purin-9-yl)-1(S),2(R)-dihydroxy-3(S)-N-[N-tert-butyloxycarbonyl(benzyloxy)amino]cyclopentane
• CAS: 210162-87-1
• 化学式: C₂₂H₂₆ClN₅O₅
• 分子量: 475.932
• InChiKey: TWVUQLFLQRWPJL-MXSMSXNCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.88
• 重原子数：
  33.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  122.83
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  5(R)-(6-chloro-9H-purin-9-yl)-1(S),2(R)-dihydroxy-3(S)-N-[N-tert-butyloxycarbonyl(benzyloxy)amino]cyclopentane 在 palladium dihydroxide 、 palladium on activated charcoal 氨 、 氢气 、 乙酰氯 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 84.5h， 生成 (1R,2S,3R,5S)-3-(6-Amino-purin-9-yl)-5-hydroxyamino-cyclopentane-1,2-diol; hydrochloride
  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 、 ruthenium trichloride 、 sodium periodate 、 偶氮二甲酸二苄酯 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 水 、 乙酸乙酯 、 乙腈 为溶剂， 反应 20.54h， 生成 5(R)-(6-chloro-9H-purin-9-yl)-1(S),2(R)-dihydroxy-3(S)-N-[N-tert-butyloxycarbonyl(benzyloxy)amino]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