(S)-2-(1-(tert-butoxycarbonylamino)-2-phenylethyl)-oxazole-4-carboxylic acid | 1004054-69-6

• 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: (S)-2-(1-(tert-butoxycarbonylamino)-2-phenylethyl)-oxazole-4-carboxylic acid
• 英文别名: 2-[(S)-alpha-[(tert-Butyloxycarbonyl)amino]phenethyl]oxazole-4-carboxylic acid；2-[(1S)-1-[(2-methylpropan-2-yl)oxycarbonylamino]-2-phenylethyl]-1,3-oxazole-4-carboxylic acid
• CAS: 1004054-69-6
• 化学式: C₁₇H₂₀N₂O₅
• 分子量: 332.356
• InChiKey: WJWOQUSJHQZWAY-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-2-(1-(tert-butoxycarbonylamino)-2-phenylethyl)-oxazole-4-carboxylic acid 在 1-羟基苯并三唑 、 N,N'-二异丙基碳二亚胺 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 、 二氯甲烷 为溶剂， 生成 2-((S)-1-amino-2-phenylethyl)-N-((S)-1-(4-carbamoyloxazol-2-yl)-2-phenylethyl)oxazole-4-carboxamide
  参考文献：
  名称：

  Parallel synthesis of bis-oxazole peptidomimetics

  摘要：

  The parallel synthesis of bis-oxazole peptidomimetics starting from Boc-aminoacids and Serine-methyl ester is described. This work presents the synthesis of oxazole aminoacid building blocks in solution phase and their utilization for the solid phase peptide synthesis of a library of diverse bis-oxazole peptidomimetics in good overall yields. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.10.078
• 作为产物：
  描述：

  Boc-Phe-Ser-OMe 在 三氯溴甲烷 、 二乙胺基三氟化硫 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 生成 (S)-2-(1-(tert-butoxycarbonylamino)-2-phenylethyl)-oxazole-4-carboxylic acid
  参考文献：
  名称：

  Parallel synthesis of bis-oxazole peptidomimetics

  摘要：

  The parallel synthesis of bis-oxazole peptidomimetics starting from Boc-aminoacids and Serine-methyl ester is described. This work presents the synthesis of oxazole aminoacid building blocks in solution phase and their utilization for the solid phase peptide synthesis of a library of diverse bis-oxazole peptidomimetics in good overall yields. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.10.078

文献信息

• Late-Stage Macrocyclization of Bioactive Peptides with Internal Oxazole Motifs via Palladium-Catalyzed C–H Olefination
  作者：Shu Liu、Chuangxu Cai、Zengbing Bai、Wangjian Sheng、Jiantao Tan、Huan Wang

  DOI：10.1021/acs.orglett.1c00580

  日期：2021.4.16

  the synthesis and direct functionalization of complex oxazole-containing peptides are in high demand. Herein, we report the late-stage site-selective functionalization of oxazole-containing peptides via palladium-catalyzed δ-C(sp2)–H olefination of phenylalanine, tryptophan, and tyrosine residues. This strategy utilizes oxazole motifs as internal directing groups and provides access to oxazole-containing

  恶唑是一种重要的药效团，存在于许多生物活性肽天然产物和肽模拟物的骨架中。对复杂的含恶唑肽的合成和直接功能化的有效方法有很高的需求。在此，我们报告了通过钯催化的苯丙氨酸、色氨酸和酪氨酸残基的δ-C(sp 2 )-H 烯化作用对含恶唑肽进行后期位点选择性功能化。该策略利用恶唑基序作为内部导向基团，并提供了获得具有生物活性的含恶唑肽大环化合物的途径。
• Combinatorial Synthesis of Oxazol-Thiazole Bis-Heterocyclic Compounds
  作者：Siva Murru、Adel Nefzi

  DOI：10.1021/co400133a

  日期：2014.1.13

  A combinatorial library of novel oxazol-thiazole bis-heterocycles was synthesized in good to excellent overall yields with high purity using a solution and solid-phase parallel synthesis approach. Oxazole amino acids, prepared from serine methyl ester and amino acids via coupling and cyclodehydration, were treated with Fmoc-NCS and alpha-haloketones for the parallel synthesis of diverse bis-heterocycles. Fmoc-isothiocyanate is used as a traceless reagent for thiazole formation. Oxazole diversity can be achieved by using variety of amino acids, whereas thiazole diversity is produced with various haloketones.