(+)-methyl (4S,5R)-4-azido-5-hydroxy-2(E)-hexenoate | 1231183-91-7

• 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 (4S,5R)-4-azido-5-hydroxy-2(E)-hexenoate
• 英文别名: methyl (E,4S,5R)-4-azido-5-hydroxyhex-2-enoate
• CAS: 1231183-91-7
• 化学式: C₇H₁₁N₃O₃
• 分子量: 185.183
• InChiKey: ZARXIHQYGFCSQL-ZRKSVAJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  60.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (+)-methyl (4S,5R)-4-azido-5-hydroxy-2(E)-hexenoate 在 三苯基膦 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 生成 methyl (E,4S,5R)-4-amino-5-hydroxyhex-2-enoate
  参考文献：
  名称：

  Total synthesis of (+) methyl β-d-vicenisaminide

  摘要：

  The total synthesis of methyl beta-D-vicenisaminide 1 has been achieved. In this approach, the synthesis of enantiomerically pure methyl (4R,5S)- and (4S,5R)-4-azido-5-hydroxy-2(E)-hexenoates 2 was established by enzymatic resolution of (+/-)-anti-5-acetoxy -4-azido-2(E)-hexenoate 4. Another stereogenic center was introduced by base-catalyzed intramolecular conjugate addition of a hemiacetal-derived alkoxide nucleophile obtained by the reaction of methyl (4S,5R)-N-4-tert-butoxycarbonyl-N-methylamino-5-hydroxyl-2(E)-hexenoate 8 and benzaldehyde in the presence of a base. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.02.014

文献信息

• Total synthesis of (+) methyl β-d-vicenisaminide
  作者：Takeru Ehara、Mikio Fujii、Machiko Ono、Hiroyuki Akita

  DOI：10.1016/j.tetasy.2010.02.014

  日期：2010.3

  The total synthesis of methyl beta-D-vicenisaminide 1 has been achieved. In this approach, the synthesis of enantiomerically pure methyl (4R,5S)- and (4S,5R)-4-azido-5-hydroxy-2(E)-hexenoates 2 was established by enzymatic resolution of (+/-)-anti-5-acetoxy -4-azido-2(E)-hexenoate 4. Another stereogenic center was introduced by base-catalyzed intramolecular conjugate addition of a hemiacetal-derived alkoxide nucleophile obtained by the reaction of methyl (4S,5R)-N-4-tert-butoxycarbonyl-N-methylamino-5-hydroxyl-2(E)-hexenoate 8 and benzaldehyde in the presence of a base. (C) 2010 Elsevier Ltd. All rights reserved.