benzyl (3S)-4-(2-hydroxyethylamino)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxobutanoate | 138582-71-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: benzyl (3S)-4-(2-hydroxyethylamino)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxobutanoate
• CAS: 138582-71-5
• 化学式: C₁₈H₂₆N₂O₆
• 分子量: 366.414
• InChiKey: VRIZPWWQPQLZHE-AWEZNQCLSA-N

物化性质

• 沸点：
  599.9±50.0 °C(Predicted)
• 密度：
  1.193±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  26
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  114
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  benzyl (3S)-4-(2-hydroxyethylamino)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxobutanoate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 benzyl (3S)-3-amino-4-(2-hydroxyethylamino)-4-oxobutanoate
  参考文献：
  名称：

  Synthesis of a peptidyldimannosyl phosphate: fragment of the variant-specific surface glycoprotein membrane anchor from trypanosoma brucei

  摘要：

  Condensation of protected beta-benzyl-aspartate 4 with 2-amino-ethanol, subsequent deprotection of the amino function and coupling with N',N'-di-benzylocarbonyl-lysine (7) afforded the peptidyl alcohol 8. Glycosylation of methyl 3,4,6 tri-O-benzyl-alpha-D-mannopyranoside (11) by ethyl 2,6-di-O-benzoyl-3,4-di-O-benzyl-1-thio-alpha-D-mannopyranoside (14) gave, after debenzoylation and protection of the 2'-hydroxyl function, the suitably protected dimannoside 21. Phosphitylation of 21 with benzyloxy-bis-(N, N-diisopropylamino)phosphine (18) followed by the addition of 8 gave, after oxidation and subsequent hydrogenolysis of the benzyl groups, the title compound in a good yield.

  DOI：

  10.1016/0040-4039(91)80242-x
• 作为产物：
  描述：

  L-天冬氨酸-4-苄酯 在 N-甲基吗啉 、 sodium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 生成 benzyl (3S)-4-(2-hydroxyethylamino)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxobutanoate
  参考文献：
  名称：

  Synthesis of a peptidyldimannosyl phosphate: fragment of the variant-specific surface glycoprotein membrane anchor from trypanosoma brucei

  摘要：

  Condensation of protected beta-benzyl-aspartate 4 with 2-amino-ethanol, subsequent deprotection of the amino function and coupling with N',N'-di-benzylocarbonyl-lysine (7) afforded the peptidyl alcohol 8. Glycosylation of methyl 3,4,6 tri-O-benzyl-alpha-D-mannopyranoside (11) by ethyl 2,6-di-O-benzoyl-3,4-di-O-benzyl-1-thio-alpha-D-mannopyranoside (14) gave, after debenzoylation and protection of the 2'-hydroxyl function, the suitably protected dimannoside 21. Phosphitylation of 21 with benzyloxy-bis-(N, N-diisopropylamino)phosphine (18) followed by the addition of 8 gave, after oxidation and subsequent hydrogenolysis of the benzyl groups, the title compound in a good yield.

  DOI：

  10.1016/0040-4039(91)80242-x

文献信息

• Synthesis of a peptidyldimannosyl phosphate: fragment of the variant-specific surface glycoprotein membrane anchor from trypanosoma brucei
  作者：R. Verduyn、J.J.A. Beliën、C.M. Dreef-Tromp、G.A. van der Marel、J.H. van Boom

  DOI：10.1016/0040-4039(91)80242-x

  日期：1991.11

  Condensation of protected beta-benzyl-aspartate 4 with 2-amino-ethanol, subsequent deprotection of the amino function and coupling with N',N'-di-benzylocarbonyl-lysine (7) afforded the peptidyl alcohol 8. Glycosylation of methyl 3,4,6 tri-O-benzyl-alpha-D-mannopyranoside (11) by ethyl 2,6-di-O-benzoyl-3,4-di-O-benzyl-1-thio-alpha-D-mannopyranoside (14) gave, after debenzoylation and protection of the 2'-hydroxyl function, the suitably protected dimannoside 21. Phosphitylation of 21 with benzyloxy-bis-(N, N-diisopropylamino)phosphine (18) followed by the addition of 8 gave, after oxidation and subsequent hydrogenolysis of the benzyl groups, the title compound in a good yield.