2-((1S,2R)-1-amino-2-hydroxypropyl)oxazole-4-carboxylic acid methyl ester | 613242-60-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-((1S,2R)-1-amino-2-hydroxypropyl)oxazole-4-carboxylic acid methyl ester
• 英文别名: methyl 2-[(1S,2R)-1-amino-2-hydroxypropyl]-1,3-oxazole-4-carboxylate
• CAS: 613242-60-7
• 化学式: C₈H₁₂N₂O₄
• 分子量: 200.194
• InChiKey: FEFNROIUTIXQMO-XINAWCOVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  98.6
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-((1S,2R)-1-amino-2-hydroxypropyl)oxazole-4-carboxylic acid methyl ester 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 生成 (S)-4-[(Z)-1-(4-Methoxycarbonyl-oxazol-2-yl)-propenylcarbamoyl]-5,2',2'-trimethyl-4',5'-dihydro-[2,4']bioxazolyl-3'-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Endoh, Nobuaki; Tsuboi, Katumasa; Kim, Riyong, Heterocycles, 2003, vol. 60, # 7, p. 1567 - 1572

  摘要：

  DOI：
• 作为产物：
  描述：

  benzyl (4S,5R)-4-[(3-methoxy-3-oxoprop-1-en-2-yl)carbamoyl]-2,2,5-trimethyl-1,3-oxazolidine-3-carboxylate 在 palladium on activated charcoal N-溴代丁二酰亚胺(NBS) 、 camphor-10-sulfonic acid 、 氢气 、 caesium carbonate 、 三氟乙酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 氯仿 、 甲苯 为溶剂， 生成 2-((1S,2R)-1-amino-2-hydroxypropyl)oxazole-4-carboxylic acid methyl ester
  参考文献：
  名称：

  Endoh, Nobuaki; Tsuboi, Katumasa; Kim, Riyong, Heterocycles, 2003, vol. 60, # 7, p. 1567 - 1572

  摘要：

  DOI：

文献信息

• Novel polyoxazole-based cyclopeptides from Streptomyces sp. Total synthesis of the cyclopeptide YM-216391 and synthetic studies towards telomestatin
  作者：Jon Deeley、Anna Bertram、Gerald Pattenden

  DOI：10.1039/b802477d

  日期：——

  hepta-oxazole 30en route to telomestatin 1. Likewise, neither the hexa-oxazole 47 or application of an intramolecular Hantzsch oxazole ring-forming reaction from 44b allowed access to the advanced polyoxazole-macrolactam intermediates 48 and 30a, respectively, towards telomestatin. Combination of the tris-oxazole based methylamine 70 with the dipeptide carboxylic acid 71 derived from D-valine and L-isoleucine

  描述了对端粒他汀（1）和YM-216391（2）中连续连接的tris-恶唑单元10、11和12的收敛，互补，合成方法。该途径涉及恶唑4-羧酸，即16a，16c，16d和恶唑2-取代的甲胺，即16b，16e，17之间的偶联反应，导致酰胺18和21，然后环脱水成相应的双恶唑恶唑啉，例如19，以及使用公认的方案进行后者的氧化。接下来，将三恶唑11和12逐步转化为六恶唑双内酰胺33。虽然双大内酰胺33（cf. 28）可以转化为相应的恶唑啉-六恶唑34和烯酰胺35，这些中间体都无法修饰成七恶唑30到端粒他汀1的途径。同样，六恶唑47或44b分子内汉茨法恶唑成环反应的应用均不能使高级聚恶唑-大环内酰胺中间体48和30a进入端粒他汀。将基于三恶唑的甲胺70与衍生自D-缬氨酸和L-异亮氨酸的二肽羧酸71结合，生成相应的酰胺，该酰胺在两个简单的步骤中转化为-氨基酸78。78的内酰胺化使用HATU，接着产生环
• Derivatization of a tris-oxazole using Pd-catalyzed coupling reactions of a 5-bromooxazole moiety
  作者：Kazuaki Shibata、Masahito Yoshida、Takayuki Doi、Takashi Takahashi

  DOI：10.1016/j.tetlet.2010.01.064

  日期：2010.3

  Modification at the C5 position of an oxazole ring contained in a 2,4-concatenated tris-oxazole by Pd-catalyzed coupling reactions was performed. Novel Pd-catalyzed amination and alkoxylation of a 5-bromooxazole derivative as well as Suzuki-Miyaura coupling and Migita-Stille coupling have been demonstrated. A wide variety of functional groups, including aryl, heteroaryl, primary and secondary amines, and phenol, were introduced in the 5-bromooxazole moiety in moderate to excellent yields using Pd(OAc)(2)/S-PHOS or Pd(OAc)(2)/X-PHOS as a catalyst. (C) 2010 Elsevier Ltd. All rights reserved.
• Synthesis and Antitumor Activity of Mechercharmycin A Analogues
  作者：Delia Hernández、Marta Altuna、Carmen Cuevas、Rosa Aligué、Fernando Albericio、Mercedes Álvarez

  DOI：10.1021/jm800513w

  日期：2008.9.25

  Several analogues of the cytotoxic thiopeptide IB-01211 or mechercharmycin A (1) have been synthesized. The cytotoxicity of 1 and the synthesized analogues were evaluated against a panel of three human tumor cell lines. Thiopeptide 1 and the most active derivatives 2 and 3c were chosen for further studies on effects on cell cycle progression and induction of apoptosis. Interestingly, the inhibition of cell division and activation of a programmed cell death by apoptosis were detected.