benzyl (3S,5S,6R)-3-[4-[(2S,3R,6R)-2,3-diphenyl-6-[2-(phenylmethoxycarbonylamino)ethyl]morpholin-4-yl]butyl]-2-oxo-5,6-diphenylmorpholine-4-carboxylate | 394251-34-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: benzyl (3S,5S,6R)-3-[4-[(2S,3R,6R)-2,3-diphenyl-6-[2-(phenylmethoxycarbonylamino)ethyl]morpholin-4-yl]butyl]-2-oxo-5,6-diphenylmorpholine-4-carboxylate
• CAS: 394251-34-4
• 化学式: C₅₄H₅₅N₃O₇
• 分子量: 858.047
• InChiKey: BDXCKKQTZRWOTI-FIQPIQNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.8
• 重原子数：
  64
• 可旋转键数：
  18
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  107
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  benzyl (3S,5S,6R)-3-[4-[(2S,3R,6R)-2,3-diphenyl-6-[2-(phenylmethoxycarbonylamino)ethyl]morpholin-4-yl]butyl]-2-oxo-5,6-diphenylmorpholine-4-carboxylate 在 palladium dichloride 氢气 作用下， 以 四氢呋喃 、 水 为溶剂， 80.0~85.0 ℃ 、551.59 kPa 条件下， 反应 6.0h， 以98%的产率得到hypusine dihydrochloride
  参考文献：
  名称：

  Asymmetric Synthesis of (+)-Hypusine

  摘要：

  [GRAPHICS]Wittig reaction of (triphenylphosphoranylidene)acetonitrile with the lactone carbonyl of (5R,6S)-4-(benzyloxycarbonyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one (3) and subsequent reduction generates morpholinylethylamine dihydrochloride (5) in quantitative yield and with excellent diastereoselectivity. Compound 5 was readily converted into hypusine dihydrochloride (1-2HCl) in overall 53% yield.

  DOI：

  10.1021/ol016959o
• 作为产物：
  描述：

  苄氧甲酸酐 在 sodium hydroxide 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 xylene 为溶剂， 反应 3.67h， 生成 benzyl (3S,5S,6R)-3-[4-[(2S,3R,6R)-2,3-diphenyl-6-[2-(phenylmethoxycarbonylamino)ethyl]morpholin-4-yl]butyl]-2-oxo-5,6-diphenylmorpholine-4-carboxylate
  参考文献：
  名称：

  Asymmetric Synthesis of (+)-Hypusine

  摘要：

  [GRAPHICS]Wittig reaction of (triphenylphosphoranylidene)acetonitrile with the lactone carbonyl of (5R,6S)-4-(benzyloxycarbonyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one (3) and subsequent reduction generates morpholinylethylamine dihydrochloride (5) in quantitative yield and with excellent diastereoselectivity. Compound 5 was readily converted into hypusine dihydrochloride (1-2HCl) in overall 53% yield.

  DOI：

  10.1021/ol016959o

文献信息

• Asymmetric Synthesis of (+)-Hypusine
  作者：Rajendra P. Jain、Brian K. Albrecht、Duane E. DeMong、Robert M. Williams

  DOI：10.1021/ol016959o

  日期：2001.12.1

  [GRAPHICS]Wittig reaction of (triphenylphosphoranylidene)acetonitrile with the lactone carbonyl of (5R,6S)-4-(benzyloxycarbonyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one (3) and subsequent reduction generates morpholinylethylamine dihydrochloride (5) in quantitative yield and with excellent diastereoselectivity. Compound 5 was readily converted into hypusine dihydrochloride (1-2HCl) in overall 53% yield.