methyl 3-azido-2,4-dihydroxy-4-phenyl-(2R,3S,4R)-butanoate | 591721-45-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 3-azido-2,4-dihydroxy-4-phenyl-(2R,3S,4R)-butanoate
• 英文别名: methyl (2R,3S,4R)-3-azido-2,4-dihydroxy-4-phenylbutanoate
• CAS: 591721-45-8
• 化学式: C₁₁H₁₃N₃O₄
• 分子量: 251.242
• InChiKey: AYPUPQMGDLCSGL-IVZWLZJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  81.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  二碳酸二叔丁酯 、 methyl 3-azido-2,4-dihydroxy-4-phenyl-(2R,3S,4R)-butanoate 在 palladium dihydroxide 氢气 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以80%的产率得到(2R,3S)-N-(tert-butoxycarbonyl)-3-amino-2-hydroxy-4-phenylbutanoic acid methyl ester
  参考文献：
  名称：

  Sulfinyl moiety as an internal nucleophile. Part 6: Stereospecific synthesis of 3-amino-2-hydroxy-4-phenylbutanoate

  摘要：

  A novel and stercospecific synthesis of (2R,3S)-3-amino-2-hydroxy-4-phenylbutanoate (AHPBA) is disclosed. The key step includes regio- and stereospecific functionalization of an alkene by the pendant sulfinyl group. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00239-8
• 作为产物：
  描述：

  methyl 5-azido-2,2-dimethyl-6-phenyl-(4R,5S,6R)-1,3-dioxane-4-carboxylate 在 camphor-10-sulfonic acid 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以85%的产率得到methyl 3-azido-2,4-dihydroxy-4-phenyl-(2R,3S,4R)-butanoate
  参考文献：
  名称：

  Sulfinyl moiety as an internal nucleophile. Part 6: Stereospecific synthesis of 3-amino-2-hydroxy-4-phenylbutanoate

  摘要：

  A novel and stercospecific synthesis of (2R,3S)-3-amino-2-hydroxy-4-phenylbutanoate (AHPBA) is disclosed. The key step includes regio- and stereospecific functionalization of an alkene by the pendant sulfinyl group. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00239-8

文献信息

• Sulfinyl moiety as an internal nucleophile. Part 6: Stereospecific synthesis of 3-amino-2-hydroxy-4-phenylbutanoate
  作者：Sadagopan Raghavan、M.Abdul Rasheed

  DOI：10.1016/s0957-4166(03)00239-8

  日期：2003.5

  A novel and stercospecific synthesis of (2R,3S)-3-amino-2-hydroxy-4-phenylbutanoate (AHPBA) is disclosed. The key step includes regio- and stereospecific functionalization of an alkene by the pendant sulfinyl group. (C) 2003 Elsevier Science Ltd. All rights reserved.