N-tert-butoxycarbonyl-L-valyl-D,L-α-methoxyglycine methyl ester | 122092-79-9

• 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: N-tert-butoxycarbonyl-L-valyl-D,L-α-methoxyglycine methyl ester
• 英文别名: Boc-L-Val-Gly(OMe)-OMe
• CAS: 122092-79-9
• 化学式: C₁₄H₂₆N₂O₆
• 分子量: 318.37
• InChiKey: DRJNTVPFLVMJEO-FTNKSUMCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  22.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  102.96
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  N-tert-butoxycarbonyl-L-valyl-D,L-α-methoxyglycine methyl ester 在 甲酸 作用下， 以90%的产率得到
  参考文献：
  名称：

  Electrogenerated chiral building blocks for diastereoselective amidoalkylation reactions

  摘要：

  已经应用了三种不同的电化学方法来合成用于二分立体选择性氨基烷基化反应的手性构建块。这些方法包括：A. 酰胺和碳酸酯的直接阳极α-甲氧基化；B. α-氨基酸衍生物的阳极甲氧基化脱羧（Hofer-Moest反应）C. 间接NaCl介导的α-氨基酸衍生物的阳极α-甲氧基化。描述了这些构建块在合成手性纯α-氨基酸、二分手性1,2-氨基醇和手性1,3-二胺中的应用。

  DOI：

  10.1051/jcp/1996930575
• 作为产物：
  描述：

  甲醇 、 N-[(1,1-二甲基乙氧基)羰基]-L-缬氨酰甘氨酸甲酯 在 sodium chloride 作用下， 以69%的产率得到N-tert-butoxycarbonyl-L-valyl-D,L-α-methoxyglycine methyl ester
  参考文献：
  名称：

  Electrogenerated chiral building blocks for diastereoselective amidoalkylation reactions

  摘要：

  已经应用了三种不同的电化学方法来合成用于二分立体选择性氨基烷基化反应的手性构建块。这些方法包括：A. 酰胺和碳酸酯的直接阳极α-甲氧基化；B. α-氨基酸衍生物的阳极甲氧基化脱羧（Hofer-Moest反应）C. 间接NaCl介导的α-氨基酸衍生物的阳极α-甲氧基化。描述了这些构建块在合成手性纯α-氨基酸、二分手性1,2-氨基醇和手性1,3-二胺中的应用。

  DOI：

  10.1051/jcp/1996930575

文献信息

• Electrogenerated chiral building blocks for diastereoselective amidoalkylation reactions
  作者：P Brungs、K Danielmeier、J Jakobi、C Nothhelfer、A Stahl、A Zietlow、E Steckhan

  DOI：10.1051/jcp/1996930575

  日期：——

  Three different electrochemical methods have been applied for the synthesis of chiral building blocks for diastereoselective amidoalkylation reactions. These are A. the direct anodic α-methoxylation of amides and carbamates; B. anodic methoxylative decarboxylation of α-amino acid derivatives (Hofer-Moest reaction) C. indirect NaCl mediated anodic α-methoxylation of α-amino acid derivatives. The application of these building blocks for the synthesis of enantiomerically pure α-amino acids, dichiral 1,2-amino alcohols and chiral 1,3-diamines is described.

  已经应用了三种不同的电化学方法来合成用于二分立体选择性氨基烷基化反应的手性构建块。这些方法包括：A. 酰胺和碳酸酯的直接阳极α-甲氧基化；B. α-氨基酸衍生物的阳极甲氧基化脱羧（Hofer-Moest反应）C. 间接NaCl介导的α-氨基酸衍生物的阳极α-甲氧基化。描述了这些构建块在合成手性纯α-氨基酸、二分手性1,2-氨基醇和手性1,3-二胺中的应用。
• Papadopoulos, Apostolos; Heyer, Joachim; Ginzel, Klaus-Dieter, Chemische Berichte, 1989, vol. 122, p. 2159 - 2164
  作者：Papadopoulos, Apostolos、Heyer, Joachim、Ginzel, Klaus-Dieter、Steckhan, Eberhard

  DOI：——

  日期：——
• Anodic oxidation of N-acyl and N-alkoxycarbonyl dipeptide esters as a key step for the formation of chiral heterocyclic synthetic building blocks
  作者：Apostolos Papadopoulos、Burhansha Lewall、Eberhard Steckhan、Klaus-Dieter Ginzel、Falk Knoch、Martin Nieger

  DOI：10.1016/s0040-4020(01)87046-0

  日期：1991.1

  The anodic oxidation of N-protected dipeptide esters using chloride as a redox catalyst can be performed regioselectively at the C-terminal amino acid. With methanol as solvent, glycine as the C-terminal, and L-valine or L-proline as N-terminal amino acid methoxylation at the glycine residue takes place. Deprotection of this product leads to the (3S,6RS)-6-methoxy-2,5-piperazinedione(3) which can be applied as a chiral cationic glycine equivalent. The exchange of the methoxy group by C-nucleophiles takes place with high trans-diastereoselectivity under steric control by the substituent in 3-position. With branched amino acids at the C-terminus of the dipeptide ester the anodic oxidation in acetonitrile/methanol (95:5) as solvent with tetraethylammonium chloride as supporting electrolyte and redox catalyst leads to methyl imidazolidin-4-one-2-carboxylates. The cyclization takes place via the intermediate formation of the N-acylimino ester of the C-terminal amino acid.
• 3-Triphenylphosphonio-2,5-piperazinediones as new chiral glycine cation equivalents
  作者：Tadeusz Gorewoda、Roman Mazurkiewicz、Wojciech Simka、Grzegorz Mlostoń、Grzegorz Schroeder、Maciej Kubicki、Nikodem Kuźnik

  DOI：10.1016/j.tetasy.2011.05.002

  日期：2011.4

  3-Triphenylphosphonio-2,5-piperazinediones were effectively synthesized from homochiral valine or proline via Boc-Val-Gly-OMe, Boc-Pro-Gly-OMe or Cbz-Pro-Gly-OMe. Retention of configuration of the primary stereogenic center of the valine and proline moieties was observed. Diastereoselective nucleophilic substitution of the triphenylphosphonium group in 2,5-piperazinediones with S-, N-, P- and C-nucleophiles was observed. The configuration of the substitution products was assigned either by their hydrolysis and decarboxylation or based on the analysis of the H-C(3)-N-H coupling constants of 3-substituted-2,5-piperazinediones derived from proline. The trans-stereoselectivity was predominant in reactions of 3-triphenylphosphonio-1,6-trimethylene-2,5-piperazinediones with the nucleophiles investigated. The stereodifferentiating ability of the proline moiety is much stronger than that of the valine unit and allowed nucleophilic alpha-functionalization of the glycine moiety with good to excellent diastereoselectivity. (C) 2011 Elsevier Ltd. All rights reserved.