N-[苄氧羰基]-D-谷氨酸 1-甲基酯 | 26566-11-0

• 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
• 中文名称: N-[苄氧羰基]-D-谷氨酸 1-甲基酯
• 中文别名: 苄氧羰基-D-谷氨酸-甲酯；N-[苄氧羰基]-D-谷氨酸1-甲基酯
• 英文名称: N-(benzyloxycarbonyl)-D-glutamic acid 1-methyl ester
• 英文别名: 1-methyl N-benzyloxycarbonyl-D-glutamate；N-Z-D-Glutamate α-methyl ester；(D)-Z-glutamic acid methyl ester；N-Cbz-D-glutamic acid 1-methyl ester；Cbz-D-Glu-OMe；Z-D-Glu-OMe；(4R)-5-methoxy-5-oxo-4-(phenylmethoxycarbonylamino)pentanoic acid
• CAS: 26566-11-0
• 化学式: C₁₄H₁₇NO₆
• 分子量: 295.292
• InChiKey: BGMCTGARFXPQML-LLVKDONJSA-N

物化性质

• 沸点：
  510.6±50.0 °C(Predicted)
• 密度：
  1.272±0.06 g/cm3(Predicted)
• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  6

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  N-[苄氧羰基]-D-谷氨酸 1-甲基酯 在 10percent Pd/C N-甲基吗啉 、 lithium hydroxide 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 氢气 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 96.0h， 生成 diammonium (N-acetyl-1,6-anhydro-muramyl)-L-alanyl-N^α-(D-isoglutamyl)-(2S,6R)-2,6-diaminopimelate
  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：

  D-谷氨酸 在 sodium methylate 、 碳酸氢钠 、 对甲苯磺酸 作用下， 以 苯 为溶剂， 生成 N-[苄氧羰基]-D-谷氨酸 1-甲基酯
  参考文献：
  名称：

  (2S,5R/2R,5S)-Aminoethylpipecolyl aepip-aegPNA chimera: synthesis and duplex/triplex stability

  摘要：

  This article reports the design and facile synthesis of novel chiral six-membered PNA analogues (2S,5R/2R,5S)-1-(N-Boc-aminoethyl)-5-(thymin-1-yl)pipecolic acid, aepipPNA IV that upon incorporation into standard aegPNA sequences effected stabilization of complexes with complementary target DNA. Substitution of aegPNA unit by the designed monomer at the C-terminus was more effective than substitution at N-terminus. The stabilizing behaviour improved with degree of substitution and was found to be dependent on their relative positions in the sequence. The six-membered piperidine ring in the design may freeze the rigid chair conformations and the relative stereochemistry of the substituents may in effect direct the complex formation with DNA/RNA by sequence-specific nucleobase recognition. In the present aepipPNA analogues, the L-trans stereochemical disposition of the substituents seems to lead to the favorable pre-organization of the PNA oligomers for complex formation with DNA. The results reported here further expand the repertoire of cyclic PNA analogues. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2004.07.080

文献信息

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  作者：Vishala Maharaj、Preeti P. Chandrachud、Wen Che、Lukasz Wojtas、Justin M. Lopchuk

  DOI：10.1021/acs.orglett.1c03344

  日期：2021.11.19

  Diazirines have been recently demonstrated to serve as electrophilic amination reagents that afford diaziridines, versatile heterocycles that are readily transformed into amines, hydrazines, and nitrogen-containing heterocycles. Here, we report the photodecarboxylative amination of redox-active esters with diazirines using inexpensive photoactivators under mild conditions with an enhanced scope for

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  DOI：10.1039/cc9960001683

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  作者：Jun-ichi Yamaguchi、Masaaki Ueki

  DOI：10.1246/cl.1996.621

  日期：1996.8

  Treatment of L-N-protected 2-amino-5-bromopentanoic acid ester, which was prepared from protected L-glutamic acid, with sodium hydride in tetrahydrofuran (THF) proceeded to give the corresponding protected L-proline in high yield. On the other hand, the reaction of 2-aminobutyric acid derivative with sodium hydride gave the 1-aminocyclopropane-1-carboxylic acid derivative.

  用四氢呋喃 (THF) 中的氢化钠处理由受保护的 L-谷氨酸制备的 LN 保护的 2-氨基-5-溴戊酸酯，以高产率得到相应的保护 L-脯氨酸。另一方面，2-氨基丁酸衍生物与氢化钠反应得到1-氨基环丙烷-1-羧酸衍生物。
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  DOI：10.1002/chem.201604279

  日期：2016.12.5

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  DOI：10.1039/b514583j

  日期：——

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