tert-butyl tert-butoxycarbonyl(9-((3aS,4R,6R,6aR)-6-((2S,5S)-5-((tert-butoxycarbonyl)amino)-6-hydroxy-2-(methoxymethoxy)hexyl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)-9H-purin-6-yl)carbamate | 1535193-09-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: tert-butyl tert-butoxycarbonyl(9-((3aS,4R,6R,6aR)-6-((2S,5S)-5-((tert-butoxycarbonyl)amino)-6-hydroxy-2-(methoxymethoxy)hexyl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)-9H-purin-6-yl)carbamate
• 英文别名: tert-butyl N-[9-[(3aS,4R,6R,6aR)-6-[(2S,5S)-6-hydroxy-2-(methoxymethoxy)-5-[(2-methylpropan-2-yl)oxycarbonylamino]hexyl]-2,2-dimethyl-4,5,6,6a-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl]purin-6-yl]-N-[(2-methylpropan-2-yl)oxycarbonyl]carbamate
• CAS: 1535193-09-9
• 化学式: C₃₆H₅₈N₆O₁₁
• 分子量: 750.89
• InChiKey: MGNGIKMOTIUNSU-UJXRQGRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  53
• 可旋转键数：
  18
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  195
• 氢给体数：
  2
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  tert-butyl tert-butoxycarbonyl(9-((3aS,4R,6R,6aR)-6-((2S,5S)-5-((tert-butoxycarbonyl)amino)-6-hydroxy-2-(methoxymethoxy)hexyl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)-9H-purin-6-yl)carbamate 在 2,2,6,6-四甲基哌啶氧化物 、 三氯异氰尿酸 、 碳酸氢钠 、 sodium bromide 作用下， 以 水 、 丙酮 为溶剂， 以79%的产率得到(2S,5S)-6-((3aR,4R,6R,6aS)-6-(6-(bis(tert-butoxycarbonyl)amino)-9H-purin-9-yl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)-2-((tert-butoxycarbonyl)amino)-5-(methoxymethoxy)hexanoic acid
  参考文献：
  名称：

  The metathesis reaction for side chain construction in carbocyclic sinefungin analogue synthesis

  摘要：

  The naturally occurring nucleoside sinefungin has found considerable use in biological investigations. More extensive sinefungin studies have been limited because few analogues have been reported due to the synthetic challenges associated with such studies. Reported herein are preparative ways to two carbocyclic sinefungin analogues: 6'-deaminocarbocyclic sinefungin and (S)-6'-hydroxy-6'-deamino-carbocyclic sinefimgin. The synthetic routes were made efficient and practical by the application of two metathesis reactions employing second generation Grubbs catalyst. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.12.030
• 作为产物：
  描述：

  9-((3aS,4R,6R,6aR)-6-((R)-2-(methoxymethoxy)but-3-en-1-yl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)-9H-purin-6-(bis-tert-butoxycarbonyl)amine 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、310.27 kPa 条件下， 反应 3.0h， 生成 tert-butyl tert-butoxycarbonyl(9-((3aS,4R,6R,6aR)-6-((2S,5S)-5-((tert-butoxycarbonyl)amino)-6-hydroxy-2-(methoxymethoxy)hexyl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)-9H-purin-6-yl)carbamate
  参考文献：
  名称：

  The metathesis reaction for side chain construction in carbocyclic sinefungin analogue synthesis

  摘要：

  The naturally occurring nucleoside sinefungin has found considerable use in biological investigations. More extensive sinefungin studies have been limited because few analogues have been reported due to the synthetic challenges associated with such studies. Reported herein are preparative ways to two carbocyclic sinefungin analogues: 6'-deaminocarbocyclic sinefungin and (S)-6'-hydroxy-6'-deamino-carbocyclic sinefimgin. The synthetic routes were made efficient and practical by the application of two metathesis reactions employing second generation Grubbs catalyst. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.12.030