Boc-Aib-Gly-OEt | 139938-01-5

• 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: Boc-Aib-Gly-OEt
• 英文别名: N-[(1,1-Dimethylethoxy)carbonyl]-2-methylalanylglycine ethyl ester；ethyl 2-[[2-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]acetate
• CAS: 139938-01-5
• 化学式: C₁₃H₂₄N₂O₅
• mdl: MFCD24391856
• 分子量: 288.344
• InChiKey: RSVLBEKPNNQKKD-UHFFFAOYSA-N

物化性质

• 沸点：
  427.7±25.0 °C(Predicted)
• 密度：
  1.088±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.769
• 拓扑面积：
  93.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  二碳酸二叔丁酯 在 sodium hydroxide 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 120.0h， 生成 Boc-Aib-Gly-OEt
  参考文献：
  名称：

  Izdebski, Jan; Kunce, Danuta; Leplawy, Miroslaw T., Polish Journal of Chemistry, 1991, vol. 65, # 7-8, p. 1427 - 1431

  摘要：

  DOI：

文献信息

• Epimerization-Free Block Synthesis of Peptides from Thioacids and Amines with the Sanger and Mukaiyama Reagents
  作者：David Crich、Indrajeet Sharma

  DOI：10.1002/anie.200805782

  日期：2009.3.16

  reaction of C‐terminal thioacids derived from protected amino acids and peptides with the Sanger reagent and other electron‐deficient aryl halides in the presence of a free amine immediately form a peptide bond with the amine. This essentially epimerization‐free method was used for the 4+4 block synthesis of a hindered octapeptide (see scheme; Boc, Pbf, and Trt are protecting groups).

  在游离胺存在下，由受保护氨基酸和肽衍生的C末端硫代酸与Sanger试剂和其他电子不足的芳基卤化物快速反应而形成的高活化硫酯立即与胺形成肽键。该基本无差向异构的方法用于受阻八肽的4 + 4嵌段合成（请参阅方案； Boc，Pbf和Trt是保护基）。
• N-hydroxypyridine-2(1H)-thione derivatives of carboxylic acids as activated esters. Part II. Applications in peptide synthesis
  作者：Derek H.R. Barton、J. Albert Ferreira

  DOI：10.1016/0040-4020(96)00488-7

  日期：1996.7

  The N-hydroxypyridine-2(1H)-thione derivatives of two urethane-protected α-amino acids readily reacted with free α-amino acid esters or the corresponding benzenesulfenamides to give simple dipeptides in reasonable yields. The benzenesulfenamides are the reagents of choice since they allowed for neutral reaction conditions and exhibited superior reactivity in sterically demanding instances. The atom-economical

  两个氨基甲酸酯保护的α-氨基酸的N-羟基吡啶-2（1 H）-硫酮衍生物容易与游离的α-氨基酸酯或相应的苯磺酰胺反应，以合理的产率得到简单的二肽。苯磺酰胺是选择的试剂，因为它们允许中性反应条件，并在空间要求严格的情况下表现出优异的反应性。Barton PTOC酯与苯磺酰胺之间的原子经济反应可提供具有合成和生物学价值的产物，并且以一致的方式进行，从而在涉及旋光性α-氨基酸残基的偶联中保持手性。
• New Reactions of the Thiocarbonyl Function. The Synthesis of Hindered Peptides
  作者：Derek H. R. Barton、J. Albert Ferreira

  DOI：10.1080/10426509708545507

  日期：1997.1.1

  chemistry of the thiocarbonyl function has been expanded to include the concerted reaction between an O-acyl derivative of N-hydroxypyridine-2(1H)-thione (a Barton PTOC ester) and a sulfenamide. The atom-economical process spawned a carboxamide and an unsymmetrical disulfide of synthetic and biological value. The reaction was successfully applied to the synthesis of sterically encumbered, urethane-protected

  摘要：众所周知的硫代羰基官能团的自由基化学已经扩展到包括 N-羟基吡啶-2（1H）-硫酮（一种巴顿 PTOC 酯）的 O-酰基衍生物和次磺酰胺之间的协同反应。原子经济过程产生了一种羧酰胺和一种具有合成和生物学价值的不对称二硫化物。该反应成功地应用于合成空间位阻、氨基甲酸酯保护的二肽。与二硫化物-膦组合相关的氧化还原技术促进了瞬态 Barton PTOC 酯的生成，结合适当的苯亚磺酰胺，苯甲酰-L-亮氨酸的 Barton PTOC 酯显示出根据敏感的 Young 测试保持光学完整性，虽然在低温下。然而，发挥作用的热力学力量非常强大，因此产量没有受到影响。除了空间要求高的情况外，母体游离胺几乎与反应时间相匹配，产率...
• Activation of carboxylic acids as their active esters by means of tert-butyl 3-(3,4-dihydrobenzotriazine-4-on)yl carbonate
  作者：Yochai Basel、Alfred Hassner

  DOI：10.1016/s0040-4039(02)00324-6

  日期：2002.4

  Carboxylic acids were activated in the presence of DMAP with tert-butyl carbonates (BOC-OX) 1, which were prepared in situ by reaction of X-OH and di-tert-butyl dicarbonate (BOC2O). The most efficient active carbonate proved to be tert-butyl 3-(3,4-dihydrobenzotriazine-4-on)yl carbonate 1a, leading to efficient formation of benzotriazinonyl esters 3 and 6, which are intermediates in reactions with primary

  羧酸是在DMAP的存在下与活化的叔丁基碳酸酯（BOC-OX）1，将其在原位X-OH和二-的反应而制备叔丁基酯（BOC 2 O）。事实证明，最有效的活性碳酸酯是碳酸3-（3,4-二氢苯并三嗪-4-on）叔丁基酯1a，可有效形成苯并三嗪壬酸酯3和6，它们是与伯胺和仲胺反应生成的中间体。以高收率得到酰胺或肽。形成3或6的副产物是对环境安全的叔丁醇（ BuOH）和一氧化碳（CO）2。受阻氨基酸AIB也以良好的产率形成二肽。
• Facile and purification free synthesis of peptides utilizing ROMPgel- and ROMPsphere-supported coupling reagents
  作者：Anthony G.M. Barrett、Brigitte Bibal、Brian T. Hopkins、Johannes Köbberling、Andrew C. Love、Livio Tedeschi

  DOI：10.1016/j.tet.2005.06.120

  日期：2005.12

  5-Norbomene-2-carboxaldehyde and norbornadiene were respectively converted into norbornene derivatives functionalized with fluoroformamidinium hexafluorophosphate and 2-bromo-N-methylpyridinium tetrafluoroborate residues. Both these norbomene monomers were ring opening metathesis polymerized or graft copolymerized onto polystyrene cores to produce ROMPgel and ROMPsphere peptide-coupling reagents. These were used to prepare hindered amides, dipeptides and tripeptides with minimal purification in parallel arrays. (c) 2005 Elsevier Ltd. All rights reserved.