(E)-(5R,6R,7S)-7-tert-Butoxycarbonylamino-6-hydroxy-5-methyl-oct-3-enoic acid methyl ester | 194143-03-8

• 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: (E)-(5R,6R,7S)-7-tert-Butoxycarbonylamino-6-hydroxy-5-methyl-oct-3-enoic acid methyl ester
• 英文别名: methyl (E,5R,6R,7S)-6-hydroxy-5-methyl-7-[(2-methylpropan-2-yl)oxycarbonylamino]oct-3-enoate
• CAS: 194143-03-8
• 化学式: C₁₅H₂₇NO₅
• 分子量: 301.383
• InChiKey: ZHKNBBJGMOIXOI-HNRYDUTKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-(5R,6R,7S)-7-tert-Butoxycarbonylamino-6-hydroxy-5-methyl-oct-3-enoic acid methyl ester 在 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 (E)-(R)-5-((4S,5R)-4-Methyl-2-oxo-oxazolidin-5-yl)-hex-3-enoic acid methyl ester
  参考文献：
  名称：

  Double stereodifferentiating crotylation reactions with α-amino aldehydes: Asymmetric synthesis of vicinal amino alcohol synthons

  摘要：

  The sense and level of 1,2-asymmetric induction have been evaluated in the BF3 . OEt2 promoted addition of (E)-crotylsilanes (R)-1 and (S)-1 to alpha-amino aldehydes 2a through 2d. The sense of carbonyl diastereoface selectivity was shown to be dependent of the chirality of the silane reagent. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01092-7
• 作为产物：
  描述：

  Boc-L-丙氨醛 、 (E)-(3R)-Methyl 3-(dimethylphenylsilyl)hex-4-enoate 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以77%的产率得到(E)-(5R,6R,7S)-7-tert-Butoxycarbonylamino-6-hydroxy-5-methyl-oct-3-enoic acid methyl ester
  参考文献：
  名称：

  Double stereodifferentiating crotylation reactions with α-amino aldehydes: Asymmetric synthesis of vicinal amino alcohol synthons

  摘要：

  The sense and level of 1,2-asymmetric induction have been evaluated in the BF3 . OEt2 promoted addition of (E)-crotylsilanes (R)-1 and (S)-1 to alpha-amino aldehydes 2a through 2d. The sense of carbonyl diastereoface selectivity was shown to be dependent of the chirality of the silane reagent. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01092-7

文献信息

• Double stereodifferentiating crotylation reactions with α-amino aldehydes: Asymmetric synthesis of vicinal amino alcohol synthons
  作者：James S. Panek、Ping Liu

  DOI：10.1016/s0040-4039(97)01092-7

  日期：1997.7

  The sense and level of 1,2-asymmetric induction have been evaluated in the BF3 . OEt2 promoted addition of (E)-crotylsilanes (R)-1 and (S)-1 to alpha-amino aldehydes 2a through 2d. The sense of carbonyl diastereoface selectivity was shown to be dependent of the chirality of the silane reagent. (C) 1997 Elsevier Science Ltd.