N^α-(benzyloxycarbonyl)-2,2-diisobutylglycine | 134173-00-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N^α-(benzyloxycarbonyl)-2,2-diisobutylglycine
• 英文别名: N-benzyloxycarbonyl di-isobutylglycine；4-Methyl-2-(2-methylpropyl)-2-(phenylmethoxycarbonylamino)pentanoic acid
• CAS: 134173-00-5
• 化学式: C₁₈H₂₇NO₄
• 分子量: 321.417
• InChiKey: AQPSUFNXAMYDMN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N^α-(benzyloxycarbonyl)-2,2-diisobutylglycine 在 氢溴酸 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成 H-Phe-Dbg-NH2*TFA
  参考文献：
  名称：

  Synthesis and conformational investigation of tetrapeptide analogues of the fragment B23-B26 of insulin

  摘要：

  Tetrapeptides containing one of a set of four different alpha,alpha-dialkyl glycines at the C-terminus were synthesized by conventional methods in solution and their conformational. behavior investigated by H-1 NMR spectroscopy in connection with molecular mechanics calculations. The results were consistent with conformations stabilized by a gamma-turn in the case of compounds with alkyl groups larger than methyl, while the corresponding Aib derivative did not exhibit intramolecular hydrogen bonding. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.07.014
• 作为产物：
  描述：

  ethyl 2,2-bis(allyl)-2-nitroacetate 在 氢氧化钾 、 三甲基氯硅烷 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 32.0h， 生成 N^α-(benzyloxycarbonyl)-2,2-diisobutylglycine
  参考文献：
  名称：

  Facile Synthesis of α,α-Diisobutylglycine and Anchoring Its Derivatives onto PAL-PEG-PS Resin

  摘要：

  alpha,alpha-Diisobutylglycine has been synthesized using a Pd-mediated dialkylation of ethyl nitroacetate as a key first step. The free alphaalphaAA is N-alpha-protected and has been applied to the assembly of conformationally constrained peptide analogues. Mixed anhydrides from BOP-Cl and Fmoc-alphaalphaAA-OH are used for anchoring alphaalphaAAs onto a trialkoxybenzyl linker on PEG-PS grafted support, upon which a beta-strand mimic with difficult sequence is assembled in a superior quality.

  DOI：

  10.1021/jo034885j

文献信息

• US5543414A
  申请人：——

  公开号：US5543414A

  公开（公告）日：1996-08-06
• Synthesis and conformational investigation of tetrapeptide analogues of the fragment B23-B26 of insulin
  作者：Lígia M. Rodrigues、José I. Fonseca、Hernâni L.S. Maia

  DOI：10.1016/j.tet.2004.07.014

  日期：2004.9

  Tetrapeptides containing one of a set of four different alpha,alpha-dialkyl glycines at the C-terminus were synthesized by conventional methods in solution and their conformational. behavior investigated by H-1 NMR spectroscopy in connection with molecular mechanics calculations. The results were consistent with conformations stabilized by a gamma-turn in the case of compounds with alkyl groups larger than methyl, while the corresponding Aib derivative did not exhibit intramolecular hydrogen bonding. (C) 2004 Elsevier Ltd. All rights reserved.
• Facile Synthesis of α,α-Diisobutylglycine and Anchoring Its Derivatives onto PAL-PEG-PS Resin
  作者：Yanwen Fu、Marcus A. Etienne、Robert P. Hammer

  DOI：10.1021/jo034885j

  日期：2003.12.1

  alpha,alpha-Diisobutylglycine has been synthesized using a Pd-mediated dialkylation of ethyl nitroacetate as a key first step. The free alphaalphaAA is N-alpha-protected and has been applied to the assembly of conformationally constrained peptide analogues. Mixed anhydrides from BOP-Cl and Fmoc-alphaalphaAA-OH are used for anchoring alphaalphaAAs onto a trialkoxybenzyl linker on PEG-PS grafted support, upon which a beta-strand mimic with difficult sequence is assembled in a superior quality.