(S)-4-<2'-(Chloroformyl)ethyl>-5-oxooxazolidin-3-carbonsaeure-benzylester | 58456-26-1

• 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: (S)-4-<2'-(Chloroformyl)ethyl>-5-oxooxazolidin-3-carbonsaeure-benzylester
• 英文别名: (S)-3-<3-(benzyloxycarbonyl)-5-oxooxazolidin-4-yl>-propanoyl chloride；(4S)-3-(benzyloxycarbonyl)-4-(3-chloro-3-oxopropyl)-1,3-oxazolidin-5-one；(S)-3-(benzyloxycarbonyl)-5-oxo-4-oxazolidinepropanoyl chloride；(S)-3-(benzyloxycarbonyl)-5-oxo-4-oxazolidinepropionyl chloride；(4S)-4-[2-(Chloroformyl)ethyl]-3-[(phenylmethoxy)carbonyl]oxazolidin-5-one；3-[(4S)-3-benzyloxycarbonyl-5-oxo-1,3-oxazolidin-4-yl]propionyl chloride；benzyl (4S)-4-(3-chloro-3-oxopropyl)-5-oxo-1,3-oxazolidine-3-carboxylate
• CAS: 58456-26-1
• 化学式: C₁₄H₁₄ClNO₅
• 分子量: 311.722
• InChiKey: XUHAAOWMUYXXDY-NSHDSACASA-N

物化性质

• 熔点：
  64-65 °C
• 沸点：
  500.4±45.0 °C(Predicted)
• 密度：
  1.365±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-4-<2'-(Chloroformyl)ethyl>-5-oxooxazolidin-3-carbonsaeure-benzylester 在 5percent Pd/BaSO₄ 盐酸 、 B-isopinocampheyl-9-borabicyclo[3.3.1]nonane 、 lutidine 、 氘 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 14.0h， 生成 DL-Β-羟基正缬氨酸
  参考文献：
  名称：

  Biosynthesis of 4-Methylproline in Cyanobacteria:  Cloning of nosE and nosF Genes and Biochemical Characterization of the Encoded Dehydrogenase and Reductase Activities

  摘要：

  The biosynthesis of the unusual amino acid 4-methylproline in the Nostoc genus of cyanobacteria was investigated on the genetic and enzymatic level. Two genes involved in the biosynthesis were cloned and the corresponding enzymes, a zinc-dependent long-chain dehydrogenase and a Delta(1)-pyrroline-5-carboxylic acid (P5C) reductase homologue, were overexpressed in Escherichia coli and biochemically characterized. Putative substrates were synthesized to test enzyme substrate specificities, and deuterium labeling studies were carried out to reveal the stereospecificities of the enzymatic reactions with respect to the substrates as well as to the coenzymes.

  DOI：

  10.1021/jo026479q
• 作为产物：
  描述：

  L-谷氨酸 在 氯化亚砜 、 2-甲基苯磺酸 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 6.5h， 生成 (S)-4-<2'-(Chloroformyl)ethyl>-5-oxooxazolidin-3-carbonsaeure-benzylester
  参考文献：
  名称：

  Nγ-Aryl glutamine analogues as probes of the ASCT2 neutral amino acid transporter binding site

  摘要：

  Analogues of L-glutamine were designed and synthesized to test a hydrogen-bond hypothesis between ligand and neutral amino acid transporter ASCT2. The key design feature contains a substituted phenyl ring on the amide nitrogen that contains electron withdrawing and electron donating groups that alter the pK(a) of the amide NH. Through this study a preliminary binding site map has been developed, and a potent commercially available competitive inhibitor of the ASCT2 transporter has been identified. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.11.028

文献信息

• Synthesis of New β-Amino Acids via 5-Oxazolidinones and the Arndt - Eistert Procedure
  作者：Andrew B. Hughes、Brad E. Sleebs

  DOI：10.1071/ch05199

  日期：——

  N-Methyl β-amino acids are potentially useful amino acid derivatives for incorporation in lead peptide therapeutics. The syntheses of five such compounds are presented. Their synthesis via 6-oxazinanones was low yielding. Alternatively, reductive cleavage of a 5-oxazolidinone gave the N-methyl α-amino acid, which was then homologated via an Arndt–Eistert procedure in high yield to give the N-methyl β-amino acid.

  N 甲基 β-氨基酸是一种潜在的有用氨基酸衍生物，可用于先导肽疗法。本文介绍了五种此类化合物的合成。通过 6-oxazinanones 合成这些化合物的产量很低。另一种方法是还原裂解 5-oxazolidinone 得到 N-甲基 α-氨基酸，然后通过 Arndt-Eistert 程序进行高产率同源反应，得到 N-甲基 β-氨基酸。
• Effective Methods for the Synthesis ofN-Methylβ-Amino Acids from All Twenty Commonα-Amino Acids Using 1,3-Oxazolidin-5-ones and 1,3-Oxazinan-6-ones
  作者：Andrew B. Hughes、Brad E. Sleebs

  DOI：10.1002/hlca.200690235

  日期：2006.11

  N-Methyl β-amino acids are generally required for application in the synthesis of potentially bioactive modified peptides and other oligomers. Previous work highlighted the reductive cleavage of 1,3-oxazolidin-5-ones to synthesise N-methyl α-amino acids. Starting from α-amino acids, two approaches were used to prepare the corresponding N-methyl β-amino acids. First, α-amino acids were converted to

  应用N-甲基β-氨基酸通常是潜在合成具有生物活性的修饰的肽和其他寡聚体的应用。先前的工作强调了1，3-恶唑烷-5-酮的还原裂解以合成N-甲基α-氨基酸。从α-氨基酸开始，使用两种方法来制备相应的N-甲基β-氨基酸。首先，α -氨基酸转化为Ñ甲基α -氨基酸由所谓的“-1,3-恶唑-5-酮的策略”，将它们再由同系阿恩特-艾斯特方法，得到Ñ-protected Ñ -甲基β -氨基酸选自20种常见衍生α -氨基酸。这些化合物的制备产率为23–57％（相对于N-甲基α-氨基酸）。在第二种方法中，可以通过Arndt–Eistert方法将12个N保护的α-氨基酸直接同源，然后将所得的β-氨基酸以30–45％的产率转化为1,3-恶二嗪-6-酮。 。最后，还原裂解以41–63％的收率提供了所需的N-甲基β-氨基酸。
• Herstellung von ?Semialdehyd?-Derivaten von Asparagins�ure- und Glutamins�ure durchRosenmund-Reduktion
  作者：Guido Bold、Heinz Steiner、Luzia Moesch、Bernhard Walliser

  DOI：10.1002/hlca.19900730219

  日期：1990.3.14

  Preparation of ‘Semialdehyde’ Derivatives of Aspartic and Glutamic Acid via the Rosenmund Reduction

  天门冬氨酸和谷氨酸的“半醛”衍生物的制备通过的罗森蒙德减少
• Constituents of microbial iron chelators. The synthesis of optically active derivatives of δ-N-hydroxy-L-ornithine.
  作者：Byung Hyun Lee、Marvin J. Miller

  DOI：10.1016/s0040-4039(01)80064-2

  日期：1984.1

  δ-N-Hydroxy-L-ornithine derivatives were synthesized from L-glutamic acid by reduction of the γ-acid chloride to the aldehyde, formation of the substituted oxime, and reductive acylation.

  通过将γ-酰氯还原为醛，形成取代的肟和还原性酰化作用，由L-谷氨酸合成δ-N-羟基-L-鸟氨酸衍生物。
• A Convenient Differential Protection Strategy for Functional Group Manipulation of Aspartic and Glutamic Acids
  作者：John M. Scholtz、Paul A. Bartlett

  DOI：10.1055/s-1989-27311

  日期：——

  Procedures are provided for selective protection of the α-carboxyl groups of aspartic and glutamic acids via the 5-oxazolidinones 2. A convenient synthesis of a differentially protected derivative of (S)-2,3-diaminopropanoic acid, 3, is described, along with examples of selective manipulation of the γ-carboxyl group of glutamic acid.

  本文提供了通过 5-噁唑烷酮 2 对天冬氨酸和谷氨酸的 δ-羧基进行选择性保护的步骤。 此外，还介绍了(S)-2,3-二氨基丙酸差异保护衍生物 3 的简便合成方法，以及选择性处理谷氨酸δ-羧基的实例。