ethyl (3aR,7S,7aS)-7-acetamido-2,2-diethyl-3a,6,7,7a-tetrahydrobenzo[d][1,3]dioxole-5-carboxylate | 1393086-04-8

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: ethyl (3aR,7S,7aS)-7-acetamido-2,2-diethyl-3a,6,7,7a-tetrahydrobenzo[d][1,3]dioxole-5-carboxylate
• CAS: 1393086-04-8
• 化学式: C₁₆H₂₅NO₅
• 分子量: 311.378
• InChiKey: IAVJEOQDPYQVFI-MJBXVCDLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.68
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  73.86
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  ethyl (3aR,7S,7aS)-7-acetamido-2,2-diethyl-3a,6,7,7a-tetrahydrobenzo[d][1,3]dioxole-5-carboxylate 在 三乙基硅烷 、 四氯化钛 、 水 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以14%的产率得到ethyl (3R,4S,5S)-5-acetamido-4-hydroxy-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate
  参考文献：
  名称：

  A concise and practical synthesis of oseltamivir phosphate(Tamiflu) from d-mannose

  摘要：

  A short and practical synthesis of oseltamivir phosphate was accomplished in 11 steps from inexpensive and abundant starting material, D-mannose. This synthetic route featured an intramolecular Horner-Wadsworth-Emmons reaction as the key step to furnish the cyclohexene ring product. The hydroxyl group was converted stereo specifically into an amino group by oxidation to the ketone and reductive amination whereas the second amino group was introduced by azide substitution of a hydroxyl group. This synthesis provided an economical and practical alternative for the synthesis of Tamiflu. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.06.065
• 作为产物：
  描述：

  ethyl 3-[(3aS,6R,6aS)-2,2-diethyl-4-hydroxy-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]-2-diethoxyphosphorylpropanoate 在 吡啶 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 2,2,6,6-四甲基哌啶氧化物 、 三氯异氰尿酸 、 盐酸羟胺 、 sodium hydride 、 molybdenum(VI) oxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 ethyl (3aR,7S,7aS)-7-acetamido-2,2-diethyl-3a,6,7,7a-tetrahydrobenzo[d][1,3]dioxole-5-carboxylate
  参考文献：
  名称：

  A concise and practical synthesis of oseltamivir phosphate(Tamiflu) from d-mannose

  摘要：

  A short and practical synthesis of oseltamivir phosphate was accomplished in 11 steps from inexpensive and abundant starting material, D-mannose. This synthetic route featured an intramolecular Horner-Wadsworth-Emmons reaction as the key step to furnish the cyclohexene ring product. The hydroxyl group was converted stereo specifically into an amino group by oxidation to the ketone and reductive amination whereas the second amino group was introduced by azide substitution of a hydroxyl group. This synthesis provided an economical and practical alternative for the synthesis of Tamiflu. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.06.065