1(R)-(6-cyclopropylamino-9H-purin-9-yl)-2(S),3(R)-dihydroxy-4(S)-N-(N-tert-butyloxycarbonylhydroxamino)cyclopentane | 210162-97-3

• 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: 1(R)-(6-cyclopropylamino-9H-purin-9-yl)-2(S),3(R)-dihydroxy-4(S)-N-(N-tert-butyloxycarbonylhydroxamino)cyclopentane
• CAS: 210162-97-3
• 化学式: C₁₈H₂₆N₆O₅
• 分子量: 406.442
• InChiKey: BQTUQPYFHAOQEC-UVLXDEKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.06
• 重原子数：
  29.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  145.86
• 氢给体数：
  4.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  1(R)-(6-cyclopropylamino-9H-purin-9-yl)-2(S),3(R)-dihydroxy-4(S)-N-(N-tert-butyloxycarbonylhydroxamino)cyclopentane 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以100%的产率得到(1R,2S,3R,5S)-3-(6-Cyclopropylamino-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 38.54h， 生成 1(R)-(6-cyclopropylamino-9H-purin-9-yl)-2(S),3(R)-dihydroxy-4(S)-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