(1R,2R,4S)-2-氨基甲酰基-4-羟甲基环戊烷羧酸 | 1025944-54-0

• 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
• 中文名称: (1R,2R,4S)-2-氨基甲酰基-4-羟甲基环戊烷羧酸
• 英文名称: (1R,2R,4S)-2-carbamoyl-4-(hydroxymethyl)cyclopentane-1-carboxylic acid
• CAS: 1025944-54-0
• 化学式: C₈H₁₃NO₄
• 分子量: 187.196
• InChiKey: NCHUAFIATQSQLP-KVQBGUIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  101
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,2R,4S)-2-氨基甲酰基-4-羟甲基环戊烷羧酸 在 吡啶 、 lead(IV) acetate 、 盐酸 、 sodium tetrahydroborate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 、 正丁醇 为溶剂， 反应 67.0h， 生成 [(1R,3R,4R)-3-[(5-amino-6-chloropyrimidin-4-yl)amino]-4-(hydroxymethyl)cyclopentyl]methanol
  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：

  (1R,5R,7R)-3-Oxabicyclo<3.2.1>octan-2-one-7-carboxylic acid 在 氨 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 (1R,2R,4S)-2-氨基甲酰基-4-羟甲基环戊烷羧酸
  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).