trans-(1R,2R)-4-Hydroxymethyl-1,2-bis(methoxycarbonyl)cyclopentane | 153759-52-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: trans-(1R,2R)-4-Hydroxymethyl-1,2-bis(methoxycarbonyl)cyclopentane
• 英文别名: dimethyl (1R,2R)-4-(hydroxymethyl)cyclopentane-1,2-dicarboxylate
• CAS: 153759-52-5
• 化学式: C₁₀H₁₆O₅
• 分子量: 216.234
• InChiKey: BYRUZJTXECMTBR-HTQZYQBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  trans-(1R,2R)-4-Hydroxymethyl-1,2-bis(methoxycarbonyl)cyclopentane 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 (1R,2R)-4-Hydroxymethyl-cyclopentane-1,2-dicarboxylic acid
  参考文献：
  名称：

  Synthesis of Carbocyclic 2',3'-Dideoxy-2'-C-hydroxymethyl Nucleosides as Potential Inhibitors of HIV

  摘要：

  The synthesis of the enantiomerically pure carbocyclic 2',3'-dideoxy-2'-C-hydroxymethyl derivatives of adenosine and guanosine is described. trans-(1R,2R)-1,2-Bis(methoxycarbonyl)-4-oxocyclopentane (4) was reacted with the zinc-dibromomethane-titanium tetrachloride mixed reagent to give an exocyclic olefin. Hydroboration followed by oxidation gave the C-2 symmetric hydroxymethyl diester 6. The two ester groups in 6 were differentiated by lactonization to give lactone 7. The lactone 7 was opened with ammonia, and the remaining carboxylic acid group was reduced. Hofmann rearrangement of the amide gave (1R,2R,4R)-2,4-bis(acetoxymethyl)-1-(tert-butoxycarbonyl)amino] cyclopentane (9), which after deprotection was converted to the adenosine derivative 12 and the guanosine derivative 15. Compounds 12 and 15 were evaluated for activity against human immunodeficiency virus (HIV).

  DOI：

  10.1021/jo00086a031
• 作为产物：
  描述：

  trans-(3R,4R)-bis(methoxycarbonyl)cyclopentanone 在 sodium hydroxide 、 dimethyl sulfide borane 、 双氧水 、 四氯化钛 、 锌 作用下， 反应 6.5h， 生成 trans-(1R,2R)-4-Hydroxymethyl-1,2-bis(methoxycarbonyl)cyclopentane
  参考文献：
  名称：

  Synthesis of Carbocyclic 2',3'-Dideoxy-2'-C-hydroxymethyl Nucleosides as Potential Inhibitors of HIV

  摘要：

  The synthesis of the enantiomerically pure carbocyclic 2',3'-dideoxy-2'-C-hydroxymethyl derivatives of adenosine and guanosine is described. trans-(1R,2R)-1,2-Bis(methoxycarbonyl)-4-oxocyclopentane (4) was reacted with the zinc-dibromomethane-titanium tetrachloride mixed reagent to give an exocyclic olefin. Hydroboration followed by oxidation gave the C-2 symmetric hydroxymethyl diester 6. The two ester groups in 6 were differentiated by lactonization to give lactone 7. The lactone 7 was opened with ammonia, and the remaining carboxylic acid group was reduced. Hofmann rearrangement of the amide gave (1R,2R,4R)-2,4-bis(acetoxymethyl)-1-(tert-butoxycarbonyl)amino] cyclopentane (9), which after deprotection was converted to the adenosine derivative 12 and the guanosine derivative 15. Compounds 12 and 15 were evaluated for activity against human immunodeficiency virus (HIV).

  DOI：

  10.1021/jo00086a031

文献信息

• Synthesis of Carbocyclic 2',3'-Dideoxy-2'-C-hydroxymethyl Nucleosides as Potential Inhibitors of HIV
  作者：Asa Rosenquist、Ingemar Kvarnstroem、Stefan C. T. Svensson、Bjoern Classon、Bertil Samuelsson

  DOI：10.1021/jo00086a031

  日期：1994.4

  The synthesis of the enantiomerically pure carbocyclic 2',3'-dideoxy-2'-C-hydroxymethyl derivatives of adenosine and guanosine is described. trans-(1R,2R)-1,2-Bis(methoxycarbonyl)-4-oxocyclopentane (4) was reacted with the zinc-dibromomethane-titanium tetrachloride mixed reagent to give an exocyclic olefin. Hydroboration followed by oxidation gave the C-2 symmetric hydroxymethyl diester 6. The two ester groups in 6 were differentiated by lactonization to give lactone 7. The lactone 7 was opened with ammonia, and the remaining carboxylic acid group was reduced. Hofmann rearrangement of the amide gave (1R,2R,4R)-2,4-bis(acetoxymethyl)-1-(tert-butoxycarbonyl)amino] cyclopentane (9), which after deprotection was converted to the adenosine derivative 12 and the guanosine derivative 15. Compounds 12 and 15 were evaluated for activity against human immunodeficiency virus (HIV).