Boc-L-Glu(OBzl)-al | 79069-53-7

• 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-L-Glu(OBzl)-al
• 英文别名: Boc-L-Glu(Bzl)-PAM resin (100-200 mesh)；benzyl (4S)-4-[(2-methylpropan-2-yl)oxycarbonylamino]-5-oxopentanoate
• CAS: 79069-53-7
• 化学式: C₁₇H₂₃NO₅
• 分子量: 321.373
• InChiKey: YXFDDMHHXOWHKA-AWEZNQCLSA-N

物化性质

• 沸点：
  467.3±45.0 °C(Predicted)
• 密度：
  1.130±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Boc-L-Glu(OBzl)-al 在 potassium tert-butylate 、 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 生成 (E)-(S)-4-Amino-hept-2-enedioic acid 7-benzyl ester 1-ethyl ester
  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：

  (S)-4-tert-Butoxycarbonylamino-4-(methoxy-methyl-carbamoyl)-butyric acid benzyl ester 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 Boc-L-Glu(OBzl)-al
  参考文献：
  名称：

  从 β-酮 γ-氨基酯合成四取代对称吡嗪：肽自二聚化的温和策略

  摘要：

  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。

  DOI：

  10.1002/ejoc.201403237

文献信息

• New methods and reagents in organic synthesis, 29, A practical method for the preparation of optically acive N-protected .ALPHA.-amino aldehydes and peptide aldehydes.
  作者：Yasumasa Hamada、Takayuki Shioiri

  DOI：10.1248/cpb.30.1921

  日期：——

  Highly optically active N-protected α-amino aldehydes and peptide aldehydes can be conveniently prepared from the corresponding β-amino alcohols with little or no racemization by the use of a combination of sulfur trioxide-pyridine complex and dimethyl-sulfoxide in the presence of triethylamine.

  高度光学活性的N-保护的α-氨基酸醛和肽醛可以通过使用硫三氧化物-吡啶复合物和二甲基亚砜的组合，在三乙胺存在下，从相应的β-氨基酸醇方便地制备，且几乎或完全不发生消旋化。
• 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。
• Preparation of protected amino aldehydes
  作者：C. Freeman Stanfield、James E. Parker、Panayiotis Kanellis

  DOI：10.1021/jo00336a039

  日期：1981.11
• Inhibition of P-glycoprotein-mediated multidrug efflux by aminomethylene and ketomethylene analogs of reversins
  作者：Ali Koubeissi、Imad Raad、Laurent Ettouati、David Guilet、Charles Dumontet、Joelle Paris

  DOI：10.1016/j.bmcl.2006.07.059

  日期：2006.11

  Several aminomethylene analogs and a ketomethylene analog of reversins were synthesized in order to evaluate their ability to inhibit P-glycoprotein-mediated drug efflux in K562/R7 human leukemic cells overexpressing P-glycoprotein. These analogs retained good activity compared to cyclosporin A and the original reversins. (c) 2006 Elsevier Ltd. All rights reserved.