tert-butyl N-[9-[(3aS,4R,6S,6aR)-6-[(E,5S)-6-hydroxy-5-[(2-methylpropan-2-yl)oxycarbonylamino]hex-3-enyl]-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 | 1535192-96-1

• 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 N-[9-[(3aS,4R,6S,6aR)-6-[(E,5S)-6-hydroxy-5-[(2-methylpropan-2-yl)oxycarbonylamino]hex-3-enyl]-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: 1535192-96-1
• 化学式: C₃₄H₅₂N₆O₉
• 分子量: 688.822
• InChiKey: NLZMIQXYIDSBLB-BGSZYQEGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  49
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  177
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[9-[(3aS,4R,6S,6aR)-6-[(E,5S)-6-hydroxy-5-[(2-methylpropan-2-yl)oxycarbonylamino]hex-3-enyl]-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 在 2,2,6,6-四甲基哌啶氧化物 、 三氯异氰尿酸 、 palladium 10% on activated carbon 、 氢气 、 碳酸氢钠 、 sodium bromide 作用下， 以 乙醇 、 水 、 丙酮 为溶剂， 20.0 ℃ 、310.27 kPa 条件下， 反应 3.0h， 生成 (S)-6-((3aR,4S,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-butoxycarbonylamino)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：

  (3aS,4S,6S,6aR)-6-(but-3-enyl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ol 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 tert-butyl N-[9-[(3aS,4R,6S,6aR)-6-[(E,5S)-6-hydroxy-5-[(2-methylpropan-2-yl)oxycarbonylamino]hex-3-enyl]-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
  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