1-[(3aS,4S,6S,6aR)-6-benzyloxy-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl]-2-[(3-chloropyrazin-2-yl)amino]ethanol

• 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: 1-[(3aS,4S,6S,6aR)-6-benzyloxy-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl]-2-[(3-chloropyrazin-2-yl)amino]ethanol
• 英文别名: 1-[(3aR,4S,6S,6aS)-2,2-dimethyl-4-phenylmethoxy-4,5,6,6a-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-6-yl]-2-[(3-chloropyrazin-2-yl)amino]ethanol
• 化学式: C₂₁H₂₆ClN₃O₄
• 分子量: 419.908
• InChiKey: UJKDEUQTWKGZPI-IEBNGJLISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  85.7
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-[(3aS,4S,6S,6aR)-6-benzyloxy-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl]-2-[(3-chloropyrazin-2-yl)amino]ethanol 在 二甲基亚砜 、 三乙胺 、 三氟乙酸酐 作用下， 以 二氯甲烷 为溶剂， 以79%的产率得到1-[(3aS,4R,6S,6aR)-6-benzyloxy-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl]-2-[(3-chloropyrazin-2-yl)amino]ethanone
  参考文献：
  名称：

  5′-Noraristeromycin C-Nucleosides Based on Imidazo[1,2-a]pyrazine

  摘要：

  The preparation of two C-5-nor-3-deazaaristeromycin diastereomeric analogues possessing a bridgehead nitrogen is described from (3aR,4R,6S,6aS)-2,2-dimethyl-6-vinyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ol that served as the cyclopentyl unit of the target carbocyclic nucleosides and as the scaffold upon which the compounds were built. The process evolved via a de novo approach for constructing the requisite fused imidazo unit between the aforementioned cyclopentyl ring and a readily available 2,3-dichloropyrazine. The syntheses were accomplished in 11 and 8 steps depending on the diastereomer sought.

  DOI：

  10.1055/s-0034-1378910
• 作为产物：
  描述：

  (+/-)-2,2-dimethyl-3αβ,6αβ-dihydro-4H-cyclopenta-1,3-dioxol-4-one 在 六甲基磷酰三胺 、 ammonium hydroxide 、 lithium aluminium tetrahydride 、 copper(I) bromide dimethylsulfide complex 、 二甲基二环氧乙烷 、 sodium hydride 、 diisopropyl (E)-azodicarboxylate 、 三乙胺 、 三苯基膦 、 sodium iodide 、 lithium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 水 、 丙酮 为溶剂， 反应 90.2h， 生成 1-[(3aS,4S,6S,6aR)-6-benzyloxy-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl]-2-[(3-chloropyrazin-2-yl)amino]ethanol
  参考文献：
  名称：

  5′-Noraristeromycin C-Nucleosides Based on Imidazo[1,2-a]pyrazine

  摘要：

  The preparation of two C-5-nor-3-deazaaristeromycin diastereomeric analogues possessing a bridgehead nitrogen is described from (3aR,4R,6S,6aS)-2,2-dimethyl-6-vinyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ol that served as the cyclopentyl unit of the target carbocyclic nucleosides and as the scaffold upon which the compounds were built. The process evolved via a de novo approach for constructing the requisite fused imidazo unit between the aforementioned cyclopentyl ring and a readily available 2,3-dichloropyrazine. The syntheses were accomplished in 11 and 8 steps depending on the diastereomer sought.

  DOI：

  10.1055/s-0034-1378910

文献信息

• 5′-Noraristeromycin C-Nucleosides Based on Imidazo[1,2-a]pyrazine
  作者：Stewart Schneller、Wei Ye

  DOI：10.1055/s-0034-1378910

  日期：——

  The preparation of two C-5-nor-3-deazaaristeromycin diastereomeric analogues possessing a bridgehead nitrogen is described from (3aR,4R,6S,6aS)-2,2-dimethyl-6-vinyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ol that served as the cyclopentyl unit of the target carbocyclic nucleosides and as the scaffold upon which the compounds were built. The process evolved via a de novo approach for constructing the requisite fused imidazo unit between the aforementioned cyclopentyl ring and a readily available 2,3-dichloropyrazine. The syntheses were accomplished in 11 and 8 steps depending on the diastereomer sought.