tert-butyl (2R,4S)-2-(tert-butyl)-4-carbamoyl-4-methyloxazolidine-3-carboxylate | 1333077-64-7

• 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: tert-butyl (2R,4S)-2-(tert-butyl)-4-carbamoyl-4-methyloxazolidine-3-carboxylate
• 英文别名: tert-butyl (2R, 4S)-2-(tert-butyl)-4-carbamoyl-4-methyl-4-methyloxazolidine-3-carboxylate；(2R,4S)-tert-butyl (2-tert-butyl-4-carbamoyl-4-methyloxazolidine)-3-carboxylate；tert-butyl (2R,4S)-2-tert-butyl-4-carbamoyl-4-methyl-1,3-oxazolidine-3-carboxylate
• CAS: 1333077-64-7
• 化学式: C₁₄H₂₆N₂O₄
• 分子量: 286.371
• InChiKey: HCOOAFPQDNFHEN-YGRLFVJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  81.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-iodo-N-(pyridin-2-yl)benzamide 、 tert-butyl (2R,4S)-2-(tert-butyl)-4-carbamoyl-4-methyloxazolidine-3-carboxylate 在 potassium phosphate 、 copper(l) iodide 、 N,N'-二甲基乙二胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 36.0h， 以81%的产率得到(2R,4S)-tert-butyl 2-(tert-butyl)-4-methyl-4-((4-(pyridin-2-ylcarbamoyl)phenyl)carbamoyl)oxazolidine-3-carboxylate
  参考文献：
  名称：

  Synthesis of Cytimidine through a One-Pot Copper-Mediated Amidation Cascade

  摘要：

  A concise synthesis of cytimidine was developed utilizing tandem Cu-mediated N-aryl amidations followed by global deprotection. This sequence exploits a regioselective coupling of an iodobenzamide with a halopyrimidine that allows the union of three fragments in a single synthetic manipulation and will permit the efficient and rapid diversification of the cytimidine core.

  DOI：

  10.1021/ol2018196
• 作为产物：
  描述：

  (2R,4S)-3-(tert-butoxycarbonyl)-2-(tert-butyl)-4-methyloxazolidine-4-carboxylic acid 在 草酰氯 、 三乙胺 、 盐酸 、 羟胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 四氢呋喃 、 水 为溶剂， 反应 8.0h， 以77%的产率得到tert-butyl (2R,4S)-2-(tert-butyl)-4-carbamoyl-4-methyloxazolidine-3-carboxylate
  参考文献：
  名称：

  Synthesis of Cytimidine through a One-Pot Copper-Mediated Amidation Cascade

  摘要：

  A concise synthesis of cytimidine was developed utilizing tandem Cu-mediated N-aryl amidations followed by global deprotection. This sequence exploits a regioselective coupling of an iodobenzamide with a halopyrimidine that allows the union of three fragments in a single synthetic manipulation and will permit the efficient and rapid diversification of the cytimidine core.

  DOI：

  10.1021/ol2018196

文献信息

• [EN] ANTIMICROBIAL COMPOUNDS<br/>[FR] COMPOSÉS ANTIMICROBIENS
  申请人：CURZA GLOBAL LLC

  公开号：WO2019013789A1

  公开（公告）日：2019-01-17

  Disclosed are compounds of formula I: or pharmaceutically acceptable salts thereof. Compounds of formula I are anti-microbials that inhibit, for instance, Mycobacterium tuberculosis (Mtb) H37Ra. Compounds of formula I also have anti-tubercular activity, exhibit limited cytotoxicity, and inhibit protein synthesis. Processes for making compounds of formula I are also disclosed, as well as methods of using compounds of formula I for the treatment of bacterial infections, particularly tuberculosis.

  公开的是I式化合物：或其药用可接受的盐。I式化合物是抗微生物的，例如抑制结核分枝杆菌（Mtb）H37Ra的。I式化合物还具有抗结核活性，表现出有限的细胞毒性，并且抑制蛋白质合成。公开了制备I式化合物的方法，以及使用I式化合物治疗细菌感染，特别是结核病的方法。
• Unifying the Aminohexopyranose‐ and Peptidyl‐Nucleoside Antibiotics: Implications for Antibiotic Design
  作者：Catherine M. Serrano、Hariprasada Reddy Kanna Reddy、Daniel Eiler、Michael Koch、Ben I. C. Tresco、Louis R. Barrows、Ryan T. VanderLinden、Charles A. Testa、Paul R. Sebahar、Ryan E. Looper

  DOI：10.1002/anie.202003094

  日期：2020.7.6

  peptidyl transferase center P‐site of the ribosome. The amicetin binding site overlaps significantly with that of the well‐known protein synthesis inhibitor balsticidin S. Amicetin, however, is the first compound structurally characterized to bind to the P‐site with demonstrated selectivity for the inhibition of prokaryotic translation. The natural product‐ribosome structure enabled the synthesis of simplified

  为了寻找与抗逆转录病毒疗法兼容的新型抗结核药，我们重新确定了阿米斯汀为先导化合物。结晶分析明确确定了阿米斯汀与嗜热栖热菌（Tth）的70S核糖体亚基的结合，揭示了其占据核糖体的肽基转移酶中心P-位点。Amicetin的结合位点与著名的蛋白质合成抑制剂balsticidin S显着重叠。然而，Amicetin是第一个在结构上表征与P位点结合的化合物，具有抑制原核生物翻译的选择性。天然产物核糖体结构使得能够合成简化的类似物，从而保留了抑制原核生物翻译的能力和选择性。
• Synthesis of Cytimidine through a One-Pot Copper-Mediated Amidation Cascade
  作者：Catherine M. Serrano、Ryan E. Looper

  DOI：10.1021/ol2018196

  日期：2011.10.7

  A concise synthesis of cytimidine was developed utilizing tandem Cu-mediated N-aryl amidations followed by global deprotection. This sequence exploits a regioselective coupling of an iodobenzamide with a halopyrimidine that allows the union of three fragments in a single synthetic manipulation and will permit the efficient and rapid diversification of the cytimidine core.