ethyl (3aR,4S,6S,7R,7aS)-7-acetamido-6-(((benzyloxy)carbonyl)amino)-2,2-diethylhexahydrobenzo[d][1,3]dioxole-4-carboxylate | 1184177-19-2

• 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: ethyl (3aR,4S,6S,7R,7aS)-7-acetamido-6-(((benzyloxy)carbonyl)amino)-2,2-diethylhexahydrobenzo[d][1,3]dioxole-4-carboxylate
• CAS: 1184177-19-2
• 化学式: C₂₄H₃₄N₂O₇
• 分子量: 462.543
• InChiKey: VBRSJEAJTCJGFJ-AFDCHOCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.67
• 重原子数：
  33.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  112.19
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  ethyl (3aR,4S,6S,7R,7aS)-7-acetamido-6-(((benzyloxy)carbonyl)amino)-2,2-diethylhexahydrobenzo[d][1,3]dioxole-4-carboxylate 在 三氟甲磺酸三甲基硅酯 、 boron fluoride-dimethyl sulfide complex 作用下， 以60%的产率得到ethyl (1S,2R,3S,4R,5S)-4-acetamido-5-(((benzyloxy)carbonyl)amino)-3-hydroxy-2-(pentan-3-yloxy)cyclohexane-1-carboxylate
  参考文献：
  名称：

  An alternative synthesis of Tamiflu®: a synthetic challenge and the identification of a ruthenium-catalyzed dihydroxylation route

  摘要：

  Synthetic studies of Tamiflu (R) and the identification of a ruthenium-catalyzed dihydroxylation route are disclosed. This newly developed synthetic process circumvents the need for a Mitsunobu inversion step and the use of explosive reagents. This route, therefore, compares favorably to the previously developed synthetic process. (C) 2009 Elsevier Ltd. All rights reserved,

  DOI：

  10.1016/j.tet.2009.05.077
• 作为产物：
  描述：

  benzyl ((3aS,4R,5S,7S,7aR)-4-acetamido-7-(((tert-butyldimethylsilyl)oxy)dicyanomethyl)-2,2-diethylhexahydrobenzo[d][1,3]dioxol-5-yl)carbamate 在 乙醇 、 triethylamine tris(hydrogen fluoride) 作用下， 以100%的产率得到ethyl (3aR,4S,6S,7R,7aS)-7-acetamido-6-(((benzyloxy)carbonyl)amino)-2,2-diethylhexahydrobenzo[d][1,3]dioxole-4-carboxylate
  参考文献：
  名称：

  An alternative synthesis of Tamiflu®: a synthetic challenge and the identification of a ruthenium-catalyzed dihydroxylation route

  摘要：

  Synthetic studies of Tamiflu (R) and the identification of a ruthenium-catalyzed dihydroxylation route are disclosed. This newly developed synthetic process circumvents the need for a Mitsunobu inversion step and the use of explosive reagents. This route, therefore, compares favorably to the previously developed synthetic process. (C) 2009 Elsevier Ltd. All rights reserved,

  DOI：

  10.1016/j.tet.2009.05.077