methyl (1R,2S,3R,4R)-4-(hydroxymethyl)-2,3-bis(phenylmethoxy)cyclopentane-1-carboxylate | 189823-66-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl (1R,2S,3R,4R)-4-(hydroxymethyl)-2,3-bis(phenylmethoxy)cyclopentane-1-carboxylate
• CAS: 189823-66-3
• 化学式: C₂₂H₂₆O₅
• 分子量: 370.445
• InChiKey: AKCJVUFJOQBWHA-NCYKPQTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (1R,2S,3R,4R)-4-(hydroxymethyl)-2,3-bis(phenylmethoxy)cyclopentane-1-carboxylate 在 硼烷 、 三甲基铝 、 氯化铵 、 silver(l) oxide 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 61.0h， 生成
  参考文献：
  名称：

  Carbocyclic Nucleoside Analogs. 1. Concise Enantioselective Synthesis of Functionalized Cyclopentanes and Formal Total Synthesis of Aristeromycin

  摘要：

  An enantioselective synthesis of functionalized cyclopentanes has been used to access carbocyclic nucleoside analogs. This pathway allows access to carbocyclic C- or carbocyclic N-nucleosides from a common intermediate, ester 16. Additionally, (1R,2R,3S,4R)-4-amino-2,3-dihydroxy-1-cyclopentanemethanol (18), an intermediate in the total synthesis of aristeromycin, has been prepared as a single enantiomer in eight isolated steps from cyclopentadiene. Progress toward the synthesis of novel carbocyclic C-nucleosides is also discussed.

  DOI：

  10.1021/jo970153d
• 作为产物：
  描述：

  ethyl (1S,2R,3R,4S,5R,6S)-3-bromo-5,6-dihydroxybicyclo[2.2.1]heptane-2-carboxylate 在 盐酸 、 sodium periodate 、 锂硼氢 、 溴 、 碳酸氢钠 、 臭氧 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 silver(l) oxide 作用下， 以 乙醚 、 水 、 苯 为溶剂， 反应 70.0h， 生成 methyl (1R,2S,3R,4R)-4-(hydroxymethyl)-2,3-bis(phenylmethoxy)cyclopentane-1-carboxylate
  参考文献：
  名称：

  Carbocyclic Nucleoside Analogs. 1. Concise Enantioselective Synthesis of Functionalized Cyclopentanes and Formal Total Synthesis of Aristeromycin

  摘要：

  An enantioselective synthesis of functionalized cyclopentanes has been used to access carbocyclic nucleoside analogs. This pathway allows access to carbocyclic C- or carbocyclic N-nucleosides from a common intermediate, ester 16. Additionally, (1R,2R,3S,4R)-4-amino-2,3-dihydroxy-1-cyclopentanemethanol (18), an intermediate in the total synthesis of aristeromycin, has been prepared as a single enantiomer in eight isolated steps from cyclopentadiene. Progress toward the synthesis of novel carbocyclic C-nucleosides is also discussed.

  DOI：

  10.1021/jo970153d

文献信息

• Carbocyclic Nucleoside Analogs. 1. Concise Enantioselective Synthesis of Functionalized Cyclopentanes and Formal Total Synthesis of Aristeromycin
  作者：Stephen J. Boyer、James W. Leahy

  DOI：10.1021/jo970153d

  日期：1997.6.13

  An enantioselective synthesis of functionalized cyclopentanes has been used to access carbocyclic nucleoside analogs. This pathway allows access to carbocyclic C- or carbocyclic N-nucleosides from a common intermediate, ester 16. Additionally, (1R,2R,3S,4R)-4-amino-2,3-dihydroxy-1-cyclopentanemethanol (18), an intermediate in the total synthesis of aristeromycin, has been prepared as a single enantiomer in eight isolated steps from cyclopentadiene. Progress toward the synthesis of novel carbocyclic C-nucleosides is also discussed.