methyl [7-methyl(2S,6R)-N^α-benzyloxycarbonyl-N^ε-(tert-butyloxycarbonyl)-2,6-diaminopimelyl]-D-alaninate | 160579-14-6

• 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 [7-methyl(2S,6R)-N^α-benzyloxycarbonyl-N^ε-(tert-butyloxycarbonyl)-2,6-diaminopimelyl]-D-alaninate
• 英文别名: methyl (2R,6S)-7-[[(2R)-1-methoxy-1-oxopropan-2-yl]amino]-2-[(2-methylpropan-2-yl)oxycarbonylamino]-7-oxo-6-(phenylmethoxycarbonylamino)heptanoate
• CAS: 160579-14-6
• 化学式: C₂₅H₃₇N₃O₉
• 分子量: 523.583
• InChiKey: SQOLYHZHQDMBQA-NZSAHSFTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  37
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  158
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl [7-methyl(2S,6R)-N^α-benzyloxycarbonyl-N^ε-(tert-butyloxycarbonyl)-2,6-diaminopimelyl]-D-alaninate 在 10percent Pd/C N-甲基吗啉 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 methyl [7-methyl (2S,6R)-N^α-(N-benzyloxycarbonyl-D-isoglutamyl α-methyl ester)-N^ε-(tert-butyloxycarbonyl)-2,6-diaminopimelyl]-D-alaninate
  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
• 作为产物：
  描述：

  (S)-4-<2'-(Chloroformyl)ethyl>-5-oxooxazolidin-3-carbonsaeure-benzylester 在 palladium dihydroxide N-甲基吗啉 、 四丁基氟化铵 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 氢气 、 双(三甲基硅烷基)氨基钾 、 碳酸氢钠 、 lithium tri-t-butoxyaluminum hydride 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 4.25h， 生成 methyl [7-methyl(2S,6R)-N^α-benzyloxycarbonyl-N^ε-(tert-butyloxycarbonyl)-2,6-diaminopimelyl]-D-alaninate
  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。
• Urethanes and ureas that induce cytokine production
  申请人：AMERICAN CYANAMID COMPANY

  公开号：EP0652228A1

  公开（公告）日：1995-05-10

  The invention relates to novel ureas and urethanes of Formula I: which stimulate cytokine production and may be used to accelerate recovery from neutropenia accompanying radio- or chemotherapy, bone marrow transplantation, or infections. Compounds in the invention or pharmaceutical compositions employing these compounds may be useful in the treatment of cancer, AIDS, aplastic anemia, myelodysplastic syndrome, and infectious diseases, and in the enhancement of immune response.

  本发明涉及式 I 的新型脲和氨酯： 它们可刺激细胞因子的产生，并可用于加速从伴随放疗或化疗、骨髓移植或感染的中性粒细胞减少症中恢复过来。本发明中的化合物或采用这些化合物的药物组合物可用于治疗癌症、艾滋病、再生障碍性贫血、骨髓增生异常综合症和传染病，以及增强免疫反应。