methyl (Z,S)-5-(3-benzyloxycarbonyl-5-oxo-1,3-oxazolidin-4-yl)-2-[(tert-butyloxycarbonyl)amino]-2-pentenoate | 160579-23-7

• 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: methyl (Z,S)-5-(3-benzyloxycarbonyl-5-oxo-1,3-oxazolidin-4-yl)-2-[(tert-butyloxycarbonyl)amino]-2-pentenoate
• 英文别名: benzyl (4S)-4-[(Z)-5-methoxy-4-[(2-methylpropan-2-yl)oxycarbonylamino]-5-oxopent-3-enyl]-5-oxo-1,3-oxazolidine-3-carboxylate
• CAS: 160579-23-7
• 化学式: C₂₂H₂₈N₂O₈
• 分子量: 448.473
• InChiKey: OZXSSWKYPAHRAX-NIFLVVHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  121
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl (Z,S)-5-(3-benzyloxycarbonyl-5-oxo-1,3-oxazolidin-4-yl)-2-[(tert-butyloxycarbonyl)amino]-2-pentenoate 在 ClO4 、 硫酰氯 四丁基氟化铵 、 氢气 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 溶剂黄146 为溶剂， 25.0 ℃ 、275.79 kPa 条件下， 生成 (2S,6R)-7-methoxy-6-[(2-methylpropan-2-yl)oxycarbonylamino]-7-oxo-2-(phenylmethoxycarbonylamino)heptanoic acid
  参考文献：
  名称：

  差异保护的内消旋-2,6-二氨基庚二酸的不对称合成

  摘要：

  由L-谷氨酸立体定向地制备了具有差异保护的2，6-二氨基庚二酸，细菌细胞壁的成分，L-赖氨酸的生物合成前体和几种合成的免疫刺激剂的成分。

  DOI：

  10.1016/0040-4039(94)88210-x
• 作为产物：
  描述：

  (S)-4-<2'-(Chloroformyl)ethyl>-5-oxooxazolidin-3-carbonsaeure-benzylester 在 双(三甲基硅烷基)氨基钾 、 lithium tri-t-butoxyaluminum hydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.25h， 生成 methyl (Z,S)-5-(3-benzyloxycarbonyl-5-oxo-1,3-oxazolidin-4-yl)-2-[(tert-butyloxycarbonyl)amino]-2-pentenoate
  参考文献：
  名称：

  Synthesis of Muramyl Peptides Containing meso-Diaminopimelic Acid

  摘要：

  Chain-extension Of L-glutamate aldehyde 3 by means of the Wittig-Homer reaction furnished the desired C-7 dicarboxylic acid derivative, which in turn, after C-C double bond hydrogenation and protecting group manipulation, afforded the 2,6-diaminopimelic acid derivatives (S,R)-9 and (S,S)-9, both with the desired orthogonal protecting group pattern. Synthesis of the muramic acid derivative 15 and attachment of an L-alanine residue furnished muramyl-L-alanine 18. The corresponding 1,6-anhydromuramic acid derivative 26 was obtained similarly. Treatment of these compounds with peptides 28-30 and with the 2,6-diaminopimelic acid containing di- and tripeptides 32a, 32b, and 35 gave the protected muramyl peptides 17, 37, 40, 42, 44, 46, and 49a and 49b, which, after deprotection, afforded the desired target molecules muramyl-L-alanine (38), muramyl-L-alanyl-D-glutamic acid (39), muramyl-L-alanyl-D-glutaminide (41), muramyl-L-alanyl-D-isoglutaminyl-L-lysine (43), muramyl-L-alanyl-D-isoglutaminyl-(2S,6R)-2,6-diaminopimelic acid (45), muramyl-L-alanylL-isoglutaminyl-(2S,6R)-2,6-dian-Anopimelinyl-D-alanine (47), 1,6-anhydromuramyl-L-alanyl-D-isoglutaminyl-(2S,6R)-2,6-diaminopimelic acid (50a), and 1,6-anhydromuramyl-L-alanyl-Disoglutaminyl-(2S,6S)-2,6-diaminiopimelic acid (50b). (C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

  DOI：

  10.1002/1099-0690(200208)2002:16<2710::aid-ejoc2710>3.0.co;2-8

文献信息

• An asymmetric synthesis of differentially protected meso-2,6-diaminopimelic acid
  作者：Ryan C. Holcomb、Steven Schow、S. Ayral-Kaloustian、Dennis Powell

  DOI：10.1016/0040-4039(94)88210-x

  日期：1994.9

  Differentially protected meso-2,6-diaminopimelic acid, a component of bacterial cell walls, a biosynthetic precursor of L-lysine and a constituent of several synthetic immunostimulants, has been prepared stereospecifically from L-glutamic acid.

  由L-谷氨酸立体定向地制备了具有差异保护的2，6-二氨基庚二酸，细菌细胞壁的成分，L-赖氨酸的生物合成前体和几种合成的免疫刺激剂的成分。
• Synthesis of Muramyl Peptides Containing meso-Diaminopimelic Acid
  作者：Niels Kubasch、Richard R. Schmidt

  DOI：10.1002/1099-0690(200208)2002:16<2710::aid-ejoc2710>3.0.co;2-8

  日期：2002.8

  Chain-extension Of L-glutamate aldehyde 3 by means of the Wittig-Homer reaction furnished the desired C-7 dicarboxylic acid derivative, which in turn, after C-C double bond hydrogenation and protecting group manipulation, afforded the 2,6-diaminopimelic acid derivatives (S,R)-9 and (S,S)-9, both with the desired orthogonal protecting group pattern. Synthesis of the muramic acid derivative 15 and attachment of an L-alanine residue furnished muramyl-L-alanine 18. The corresponding 1,6-anhydromuramic acid derivative 26 was obtained similarly. Treatment of these compounds with peptides 28-30 and with the 2,6-diaminopimelic acid containing di- and tripeptides 32a, 32b, and 35 gave the protected muramyl peptides 17, 37, 40, 42, 44, 46, and 49a and 49b, which, after deprotection, afforded the desired target molecules muramyl-L-alanine (38), muramyl-L-alanyl-D-glutamic acid (39), muramyl-L-alanyl-D-glutaminide (41), muramyl-L-alanyl-D-isoglutaminyl-L-lysine (43), muramyl-L-alanyl-D-isoglutaminyl-(2S,6R)-2,6-diaminopimelic acid (45), muramyl-L-alanylL-isoglutaminyl-(2S,6R)-2,6-dian-Anopimelinyl-D-alanine (47), 1,6-anhydromuramyl-L-alanyl-D-isoglutaminyl-(2S,6R)-2,6-diaminopimelic acid (50a), and 1,6-anhydromuramyl-L-alanyl-Disoglutaminyl-(2S,6S)-2,6-diaminiopimelic acid (50b). (C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.