(S)-4-tert-Butoxycarbonylamino-4-(methoxy-methyl-carbamoyl)-butyric acid benzyl ester | 497830-99-6

• 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-tert-Butoxycarbonylamino-4-(methoxy-methyl-carbamoyl)-butyric acid benzyl ester
• 英文别名: benzyl (4S)-5-[methoxy(methyl)amino]-4-[(2-methylpropan-2-yl)oxycarbonylamino]-5-oxopentanoate
• CAS: 497830-99-6
• 化学式: C₁₉H₂₈N₂O₆
• 分子量: 380.441
• InChiKey: LOWZQRSKJMCQQK-HNNXBMFYSA-N

物化性质

• 密度：
  1.150±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  27
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  94.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-4-tert-Butoxycarbonylamino-4-(methoxy-methyl-carbamoyl)-butyric acid benzyl ester 在 lithium aluminium tetrahydride 、 potassium tert-butylate 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 7-O-benzyl 1-O-ethyl (E,4S)-4-(benzylamino)hept-2-enedioate
  参考文献：
  名称：

  Synthesis of densely functionalized pyrrolidinone templates by an intramolecular oxo-Diels–Alder reaction

  摘要：

  Preparation of densely functionalized pyrrolidinone templates, is a challenge for synthetic chemists. These templates are important building blocks for novel conformationally constrained natural products or for library generation of highly functionalized bi or polycyclic compounds. We discovered that trienes 6a-j undergo facile stereoselective intramolecular Diels-Alder reactions to generate densely functionalized cis fused pyrrolidinone templates 1a-j. These reactions allow for directed remote hydroxylation with complete control of stereochemistry. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01711-2
• 作为产物：
  描述：

  N-叔丁氧羰基-L-谷氨酸 5-苄酯 、 二甲羟胺盐酸盐 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 生成 (S)-4-tert-Butoxycarbonylamino-4-(methoxy-methyl-carbamoyl)-butyric acid benzyl ester
  参考文献：
  名称：

  使用亚硝基连续流光化学重排进行肽片段偶联

  摘要：

  顺其自然通过被描述硝酮的连续流动光化学重排的方式（参见方案）用于酰胺键形成的一般方法：。简单的芳基-烷基酰胺键以及复杂的肽键可在不到20分钟的停留时间内高效构建。用这种方法合成了四肽，该方法可用于肽片段的偶联。

  DOI：

  10.1002/anie.201300504

文献信息

• Peptide Fragment Coupling Using a Continuous-Flow Photochemical Rearrangement of Nitrones
  作者：Yuan Zhang、Melissa L. Blackman、Andrew B. Leduc、Timothy F. Jamison

  DOI：10.1002/anie.201300504

  日期：2013.4.8

  amide bond formation by way of a continuous‐flow photochemical rearrangement of nitrones was described (see scheme). Simple aryl‐alkyl amide bonds as well as complex peptide bonds were constructed efficiently with a residence time less than 20 minutes. A tetrapeptide was synthesized in this way and the method could be applied to peptide fragment coupling.

  顺其自然通过被描述硝酮的连续流动光化学重排的方式（参见方案）用于酰胺键形成的一般方法：。简单的芳基-烷基酰胺键以及复杂的肽键可在不到20分钟的停留时间内高效构建。用这种方法合成了四肽，该方法可用于肽片段的偶联。
• Synthesis of Tetrasubstituted Symmetrical Pyrazines from β-Keto γ-Amino Esters: A Mild Strategy for Self-Dimerization of Peptides
  作者：Mothukuri Ganesh Kumar、Varsha J. Thombare、Rupal D. Bhaisare、Anindita Adak、Hosahudya N. Gopi

  DOI：10.1002/ejoc.201403237

  日期：2015.1

  facile synthesis of highly symmetrical tetrasubstituted pyrazines through simple aerial oxidation of β-keto γ-amino esters is reported. The scope of the reaction was examined by use of various amino acid side-chain functional groups and peptides. The mild and efficient transformation of β-keto γ-amino esters into pyrazines may serve as an attractive strategy for self-dimerization of peptides.

  报道了通过 β-酮基 γ-氨基酯的简单空气氧化轻松合成高度对称的四取代吡嗪。通过使用各种氨基酸侧链官能团和肽来检查反应范围。β-酮基γ-氨基酯温和有效地转化为吡嗪类化合物可以作为一种有吸引力的肽自二聚化策略。
• Beta-sheet mimetics and use thereof as inhibitors of biologically active peptides or proteins
  申请人：Kahn Michael

  公开号：US20060276408A1

  公开（公告）日：2006-12-07

  There are disclosed β-sheet mimetics and methods relating to the same for imparting or stabilizing the β-sheet structure of a peptide, protein or molecule. In one aspect, β-sheet mimetics are disclosed having utility as protease inhibitors in general and, more specifically, as serine protease inhibitors such as thrombin, elastase and Factor X inhibitors. In one embodiment, the β-sheet mimetic is a thrombin inhibitor.

  本发明揭示了β-折叠结构类似物及其相关方法，用于赋予或稳定肽、蛋白质或分子的β-折叠结构。在一个方面，本发明揭示了具有普遍作为蛋白酶抑制剂的效用的β-折叠结构类似物，更具体地说，是丝氨酸蛋白酶抑制剂，如凝血酶、弹性蛋白酶和X因子抑制剂。在一个实施例中，β-折叠结构类似物是凝血酶抑制剂。
• Efficient synthesis of N-protected amino/peptide Weinreb amides from T3P and DBU
  作者：K.M. Sharnabai、G. Nagendra、T.M. Vishwanatha、Vommina V. Sureshbabu

  DOI：10.1016/j.tetlet.2012.11.064

  日期：2013.2

  The reaction of N-alpha-protected amino/peptide acid with N,O-dimethylhydroxylamine hydrochloride in the presence of T3P and DBU to obtain enantiomerically pure N-alpha-protected amino/peptidyl Weinreb amides in high yields has been described. Fmoc-Ala-Weinreb amide 2a is obtained as single crystal, and its structure was determined through X-ray crystallography. (C) 2012 Elsevier Ltd. All rights reserved.
• US7511039B2
  申请人：——

  公开号：US7511039B2

  公开（公告）日：2009-03-31