3(S)-trans-3,4-Bis<(benzoyloxy)methyl>cyclopentanone oxime | 158214-39-2

• 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: 3(S)-trans-3,4-Bis<(benzoyloxy)methyl>cyclopentanone oxime
• 英文别名: 3(S)-trans-3,4-Bis[(benzoyloxy)methyl]cyclopentanone oxime；[(1S,2S)-2-(benzoyloxymethyl)-4-hydroxyiminocyclopentyl]methyl benzoate
• CAS: 158214-39-2
• 化学式: C₂₁H₂₁NO₅
• 分子量: 367.401
• InChiKey: VKAQJDVZTOZYKM-QZTJIDSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  85.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3(S)-trans-3,4-Bis<(benzoyloxy)methyl>cyclopentanone oxime 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以43%的产率得到(1β,3α,4β)-3,4-Bis(hydroxymethyl)-1-cyclopentylamine
  参考文献：
  名称：

  A Novel Approach toward the Synthesis of Chiral 2,3-Dideoxy Nucleosides and Their Carbocyclic Analogs

  摘要：

  Photochemical ring-expansion of chiral 2(S),3(R)-bis[(benzoyloxy) methyl] cyclobutanone (3) in the presence of alcohols and acidic N-H functional groups gives anomeric mixtures of acetals and N-amino acetals, respectively, with retention of stereochemistry of the ring substituents. In the presence of purine and 6-chloropurine the corresponding protected nucleosides are-obtained. The photoadduct with 6-chloropurine is converted to the known medicinally active deprotected adenine nucleoside with methanolic ammonia. One-carbon homologation of ketone 3 with diazomethane produces the corresponding optically pure cyclopentanone 8 with retention of stereochemistry. This ketone is converted to the optically pure cyclopentylamine 10 in two steps. Racemic amine 10 has been used as a key intermediate in the preparation of carbocyclic nucleosides.

  DOI：

  10.1021/jo00087a029
• 作为产物：
  描述：

  (1S,2S)-3,3-二甲氧基-1,2-环丁烷二甲醇 在 吡啶 、 硫酸 、 盐酸羟胺 作用下， 以 甲醇 、 乙醚 、 乙醇 、 乙腈 为溶剂， 反应 35.5h， 生成 3(S)-trans-3,4-Bis<(benzoyloxy)methyl>cyclopentanone oxime
  参考文献：
  名称：

  A Novel Approach toward the Synthesis of Chiral 2,3-Dideoxy Nucleosides and Their Carbocyclic Analogs

  摘要：

  Photochemical ring-expansion of chiral 2(S),3(R)-bis[(benzoyloxy) methyl] cyclobutanone (3) in the presence of alcohols and acidic N-H functional groups gives anomeric mixtures of acetals and N-amino acetals, respectively, with retention of stereochemistry of the ring substituents. In the presence of purine and 6-chloropurine the corresponding protected nucleosides are-obtained. The photoadduct with 6-chloropurine is converted to the known medicinally active deprotected adenine nucleoside with methanolic ammonia. One-carbon homologation of ketone 3 with diazomethane produces the corresponding optically pure cyclopentanone 8 with retention of stereochemistry. This ketone is converted to the optically pure cyclopentylamine 10 in two steps. Racemic amine 10 has been used as a key intermediate in the preparation of carbocyclic nucleosides.

  DOI：

  10.1021/jo00087a029

文献信息

• A Novel Approach toward the Synthesis of Chiral 2,3-Dideoxy Nucleosides and Their Carbocyclic Analogs
  作者：Edward Lee-Ruff、Wei-Qin Wan、Ji-Long Jiang

  DOI：10.1021/jo00087a029

  日期：1994.4

  Photochemical ring-expansion of chiral 2(S),3(R)-bis[(benzoyloxy) methyl] cyclobutanone (3) in the presence of alcohols and acidic N-H functional groups gives anomeric mixtures of acetals and N-amino acetals, respectively, with retention of stereochemistry of the ring substituents. In the presence of purine and 6-chloropurine the corresponding protected nucleosides are-obtained. The photoadduct with 6-chloropurine is converted to the known medicinally active deprotected adenine nucleoside with methanolic ammonia. One-carbon homologation of ketone 3 with diazomethane produces the corresponding optically pure cyclopentanone 8 with retention of stereochemistry. This ketone is converted to the optically pure cyclopentylamine 10 in two steps. Racemic amine 10 has been used as a key intermediate in the preparation of carbocyclic nucleosides.