tert-butyl ((2R)-1-((tert-butyldimethylsilyl)oxy)-3-hydroxypent-4-en-2-yl)carbamate | 736143-66-1

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: tert-butyl ((2R)-1-((tert-butyldimethylsilyl)oxy)-3-hydroxypent-4-en-2-yl)carbamate
• 英文别名: tert-butyl 1-(tert-butyldimethylsilyloxy)-3-hydroxypent-4-en-2-ylcarbamate
• CAS: 736143-66-1
• 化学式: C₁₆H₃₃NO₄Si
• 分子量: 331.528
• InChiKey: NGIPSDYTERGUEU-PZORYLMUSA-N

物化性质

• 沸点：
  399.1±42.0 °C(Predicted)
• 密度：
  0.973±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.45
• 重原子数：
  22.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  67.79
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  tert-butyl ((2R)-1-((tert-butyldimethylsilyl)oxy)-3-hydroxypent-4-en-2-yl)carbamate 在 N-甲基吗啉 、 盐酸 、 sodium hypochlorite 、 氯磺酰异氰酸酯 、 titanium(III) chloride 、 2,2,6,6-四甲基哌啶氧化物 、 偶氮二甲酸二异丙酯 、 盐酸羟胺 、 ammonium acetate 、 碳酸氢钠 、 potassium carbonate 、 三苯基膦 、 三氟乙酸 、 potassium hydroxide 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 为溶剂， 反应 4.59h， 生成 tert-butyl 2-((Z)-1-(2-(tert-butoxycarbonylamino)thiazol-4-yl)-2-((3S,4S)-1-(3-(5-hydroxy-4-oxo-1,4-dihydropyridin-2-yl)-4-(3-(methylsulfonyl)propyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-ylsulfonylcarbamoyl)-2-oxo-4-vinylazetidin-3-ylamino)-2-oxoethylideneaminooxy)-2-methylpropanoate
  参考文献：
  名称：

  SAR and Structural Analysis of Siderophore-Conjugated Monocarbam Inhibitors of Pseudomonas aeruginosa PBP3

  摘要：

  A main challenge in the development of new agents for the treatment of Pseudomonas aeruginosa infections is the identification of chemotypes that efficiently penetrate the cell envelope and are not susceptible to established resistance mechanisms. Siderophore-conjugated monocarbams are attractive because of their ability to hijack the bacteria's iron uptake machinery for transport into the periplasm and their inherent stability to metallo-beta-lactamases. Through development of the SAR we identified a number of modifications to the scaffold that afforded active anti-P. aeruginosa agents with good physicochemical properties. Through crystallographic efforts we gained a better understanding into how these compounds bind to the target penicillin binding protein PBP3 and factors to consider for future design.

  DOI：

  10.1021/acsmedchemlett.5b00026
• 作为产物：
  描述：

  2-(tert-butoxycarbonylamino)-3-hydroxypropionic acid methyl ester 在 咪唑 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 5.0h， 生成 tert-butyl ((2R)-1-((tert-butyldimethylsilyl)oxy)-3-hydroxypent-4-en-2-yl)carbamate
  参考文献：
  名称：

  SAR and Structural Analysis of Siderophore-Conjugated Monocarbam Inhibitors of Pseudomonas aeruginosa PBP3

  摘要：

  A main challenge in the development of new agents for the treatment of Pseudomonas aeruginosa infections is the identification of chemotypes that efficiently penetrate the cell envelope and are not susceptible to established resistance mechanisms. Siderophore-conjugated monocarbams are attractive because of their ability to hijack the bacteria's iron uptake machinery for transport into the periplasm and their inherent stability to metallo-beta-lactamases. Through development of the SAR we identified a number of modifications to the scaffold that afforded active anti-P. aeruginosa agents with good physicochemical properties. Through crystallographic efforts we gained a better understanding into how these compounds bind to the target penicillin binding protein PBP3 and factors to consider for future design.

  DOI：

  10.1021/acsmedchemlett.5b00026

文献信息

• Asymmetric Synthesis of the Balanol Heterocycle via a Palladium-Mediated Epimerization and Olefin Metathesis
  作者：Gregory R. Cook、P. Sathya Shanker、Scott L. Peterson

  DOI：10.1021/ol990705+

  日期：1999.8.1

  utilizing a Pd-catalyzed equilibration of diastereomeric 5-vinyloxazolines to set the stereochemistry of the vicinal amino and hydroxyl groups. A ruthenium-catalyzed ring-closing metathesis was employed to form the seven-membered nitrogen heterocyle.

  一种有效的蛋白激酶C抑制剂balanol的对映选择性形式合成，是通过D-丝氨酸利用Pd催化的非对映体5-乙烯基恶唑啉的平衡来设定邻位氨基和羟基的立体化学而完成的。钌催化的闭环复分解被用来形成七元氮杂环。
• Nitrogen Heterocycles via Palladium-Catalyzed Carbocyclization. Formal Synthesis of (+)-α-Allokainic Acid
  作者：Gregory R. Cook、Liangdong Sun

  DOI：10.1021/ol049087+

  日期：2004.7.1

  investigated and found to be highly dependent on the phosphine ligand as well as the presence of coordinating counterions. Nitrogen heterocycles were formed without erosion of the stereochemical integrity. The utility of the lactam products was demonstrated by the formal synthesis of (+)-alpha-allokainic acid.

  [反应：见正文]研究了Pd催化的酮酰胺的碳环化，并高度依赖于膦配体以及配位抗衡离子的存在。在不破坏立体化学完整性的情况下形成了氮杂环。内酰胺产品的效用通过（+）-α-链烷二酸的正式合成得到证明。
• Total synthesis of deoxymannojirimycin and d-mannolactam via carbonylation of 5-vinyloxazolidin-2-ones
  作者：Julian G Knight、Kirill Tchabanenko

  DOI：10.1016/s0040-4020(02)01534-x

  日期：2003.1

  The stereoselective synthesis of piperidine alkaloids deoxymannojirimycin and D-mannolactam. from D-serine has been achieved. The key step involves palladium-catalysed decarboxylative carbonylation of a serine-derived 5-vinyloxazolidin-2-one to give 6-(tert-butyldimethylsilyloxymethyl)-3,6-dihydro-1H-pyridin-2-one which was subsequently converted into the title compounds. (C) 2003 Elsevier Science Ltd. All rights reserved.