(S)-2-((1S,2S)-1-((tert-butoxycarbonyl)amino)-2-methylbutyl)-4,5-dihydrooxazole-4-carboxylic acid methyl ester | 910468-13-2

• 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)-2-((1S,2S)-1-((tert-butoxycarbonyl)amino)-2-methylbutyl)-4,5-dihydrooxazole-4-carboxylic acid methyl ester
• 英文别名: 2-[1'(S)-(tert-butyloxycarbonylamino)-2'(S)-methylbutyl]-4(S)-(methoxycarbonyl)oxazoline
• CAS: 910468-13-2
• 化学式: C₁₅H₂₆N₂O₅
• 分子量: 314.382
• InChiKey: PEAVDRYCSQDPHI-DCAQKATOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  86.22
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (S)-2-((1S,2S)-1-((tert-butoxycarbonyl)amino)-2-methylbutyl)-4,5-dihydrooxazole-4-carboxylic acid methyl ester 在 lithium hydroxide 、 三氯溴甲烷 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 7.0h， 生成 2-[1'(S)-(tert-butyloxycarbonylamino)-2'(S)-methylbutyl]-4-carboxyoxazole
  参考文献：
  名称：

  Rational Design of Bacitracin A Derivatives by Incorporating Natural Product Derived Heterocycles

  摘要：

  Heterocycles display common structural motifs in nonribosomally produced peptides with an enormous impact on their bioactivity. In the case of the branched cyclic Bacitracin A, the thiazoline moiety is manufactured during NRPS peptide chain elongation. Here we describe a method to selectively alter the heterocyclic metal binding subunit of Bacitracin A by the synthesis of heterocyclic building blocks that were successfully coupled to the linear decapeptide and subsequently cyclized using the excised bacitracin PCP-TE bidomain. Utilization of this cyclase allowed the first generation of branched cyclic bacitracin derivatives containing thiazole and oxazoles. The generated bacitracin derivatives showed bactericidal activity, indicating the possibility of altering the biological important heterocyclic subunit and overcoming existing limitations for the application of bacitracin.

  DOI：

  10.1021/ja062906w
• 作为产物：
  描述：

  L-异亮氨酸 在 二乙胺基三氟化硫 、 1-羟基苯并三唑 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 2.5h， 生成 (S)-2-((1S,2S)-1-((tert-butoxycarbonyl)amino)-2-methylbutyl)-4,5-dihydrooxazole-4-carboxylic acid methyl ester
  参考文献：
  名称：

  Total synthesis of the azolemycins

  摘要：

  新发现的多唑类天然产物azolemycins A-D的首次全合成，以及四氧唑非天然类似物的合成被描述。

  DOI：

  10.1039/c5ob02520f

文献信息

• The rapid synthesis of oxazolines and their heterogeneous oxidation to oxazoles under flow conditions
  作者：Steffen Glöckner、Duc N. Tran、Richard J. Ingham、Sabine Fenner、Zoe E. Wilson、Claudio Battilocchio、Steven V. Ley

  DOI：10.1039/c4ob02105c

  日期：——

  A rapid flow synthesis of oxazolines and their oxidation to the corresponding oxazoles is reported. The oxazolines are prepared at room temperature in a stereospecific manner, with inversion of stereochemistry, from β-hydroxy amides using Deoxo-Fluor®. The corresponding oxazoles can then be obtained via a packed reactor containing commercial manganese dioxide.

  报道了恶唑啉的快速流合成及其氧化成相应的恶唑。恶唑啉是在室温下使用Deoxo-Fluor®由β-羟基酰胺以立体有择的方式通过立体化学的方式从β-羟基酰胺制备的。然后可以通过包含市售二氧化锰的填充反应器获得相应的恶唑。
• Synthesis of a Microcystis aeruginosa predicted metabolite with antimalarial activity
  作者：Stella Peña、Laura Scarone、Eduardo Manta、Lindsay Stewart、Vanessa Yardley、Simon Croft、Gloria Serra

  DOI：10.1016/j.bmcl.2012.06.028

  日期：2012.8

  The synthesis of a Microcystis aeruginosa predicted metabolite analog of aerucyclamide B was performed. This hexacyclopeptide was obtained from three heterocyclic building blocks by a convergent macrocycle-assembly methodology. The compound exhibited good in vitro antiplasmodial activity (IC50: 0.18 mu M, K1, cholorquine resistant strain). (c) 2012 Elsevier Ltd. All rights reserved.