4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside | 1295649-89-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside
• 英文别名: [(2R,3S,4S,5R,6R)-4,5-diacetoxy-6-(acetoxymethyl)-2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]tetrahydropyran-3-yl] acetate；4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl 2,3,4,6-tetra-O-acetyl-alpha-D-mannopyranoside；[(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]oxan-2-yl]methyl acetate
• CAS: 1295649-89-6
• 化学式: C₂₆H₃₅BO₁₂
• 分子量: 550.368
• InChiKey: YLXKXHWNSZVVHW-DJCPXJLLSA-N

物化性质

• 沸点：
  598.3±50.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.45
• 重原子数：
  39
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  142
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 在 四(三苯基膦)钯 、 sodium methylate 甲醇 、 caesium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 1.0h， 生成 methyl 5-[4-(α-D-mannopyranosyloxy)phenyl]pyridine-3-carboxylate
  参考文献：
  名称：

  [EN] COMPOUNDS AND METHODS FOR TREATING BACTERIAL INFECTIONS
  [FR] COMPOSÉS ET MÉTHODES POUR LE TRAITEMENT D'INFECTIONS BACTÉRIENNES

  摘要：

  本发明包括用于治疗尿路感染的化合物和方法。

  公开号：

  WO2011050323A1
• 作为产物：
  描述：

  2,3,4,6-四-O-乙酰基吡喃己糖 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 三氟甲磺酸三甲基硅酯 、 potassium acetate 、 caesium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 8.0h， 生成 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside
  参考文献：
  名称：

  [EN] MANNOSE DERIVATIVES AS ANTAGONISTS OF BACTERIAL ADHESION
  [FR] DÉRIVÉS DE MANNOSE UTILISÉS EN TANT QU'ANTAGONISTES DE L'ADHÉSION BACTÉRIENNE

  摘要：

  公开号：

  WO2011073112A3

文献信息

• [EN] MANNOSIDE COMPOUNDS AND METHODS OF USE THEREOF<br/>[FR] COMPOSÉS MANNOSIDES ET LEURS PROCÉDÉS D'UTILISATION
  申请人：UNIV WASHINGTON

  公开号：WO2012109263A1

  公开（公告）日：2012-08-16

  The present invention encompasses compounds and methods for treating urinary tract infections.

  本发明涵盖了用于治疗尿路感染的化合物和方法。
• Improving the Switching Capacity of Glyco‐Self‐Assembled Monolayers on Au(111)
  作者：Ellen Fast、Alexander Schlimm、Irene Lautenschläger、Kai Uwe Clausen、Thomas Strunskus、Carina Spormann、Thisbe K. Lindhorst、Felix Tuczek

  DOI：10.1002/chem.201903644

  日期：2020.1.7

  synthesized through a modular approach, and the respective glyco-SAMs were fabricated on Au(111). Their photoswitching properties have been extensively investigated by applying a powerful set of methods (IRRAS, XPS, and NEXAFS). Indeed, the combination of tailor-made biaryl-azobenzene glycosides and suitable diluent molecules led to photoswitchable glyco-SAMs with a significantly enhanced and unprecedented switching

  用光致异构化偶氮苯糖苷修饰的自组装单层 (SAM) 是研究配体方向对碳水化合物识别影响的有用工具。然而，SAM 在两种特定状态之间进行光切换的特点是容量有限。本研究的目标是改进光开关偶氮苯糖-SAM。已经研究了不同的概念，特别是自稀释和刚性联芳基主链。通过模块化方法合成了所需的 SH 功能化偶氮苯糖复合物，并在 Au(111) 上制备了相应的糖-SAM。通过应用一组强大的方法（IRRAS、XPS 和 NEXAFS），它们的光开关特性得到了广泛的研究。事实上，定制的联芳基偶氮苯糖苷和合适的稀释剂分子的组合产生了具有显着增强和前所未有的开关能力的光可开关糖-SAM。
• MANNOSE DERIVATIVES AS ANTAGONISTS OF BACTERIAL ADHESION
  申请人：Ernst Beat

  公开号：US20120270824A1

  公开（公告）日：2012-10-25

  Compounds of the formula (I) wherein n is 0, 1 or 2, R 1 is aryl, heteroaryl or heterocyclyl, and R 2 and R 3 are hydrogen or a substituent as described in the specification, are useful for the prevention and treatment of bacterial infections, in particular of urinary infections caused by E. coli .

  式(I)的化合物，其中n为0、1或2，R1为芳基、杂芳基或杂环基，R2和R3为氢或规范中所述的取代基，对于预防和治疗细菌感染，特别是由大肠杆菌引起的尿路感染是有用的。
• Lead Optimization Studies on FimH Antagonists: Discovery of Potent and Orally Bioavailable Ortho-Substituted Biphenyl Mannosides
  作者：Zhenfu Han、Jerome S. Pinkner、Bradley Ford、Erik Chorell、Jan M. Crowley、Corinne K. Cusumano、Scott Campbell、Jeffrey P. Henderson、Scott J. Hultgren、James W. Janetka

  DOI：10.1021/jm300165m

  日期：2012.4.26

  Herein, we describe the X-ray structure-based design and optimization of biaryl mannoside FimH inhibitors. Diverse modifications to the biaryl ring to improve druglike physical and pharmacokinetic properties of mannosides were assessed for FimH binding affinity based on their effects on hemagglutination and biofilm formation along with direct FimH binding assays. Substitution on the mannoside phenyl ring ortho to the glycosidic bond results in large potency enhancements several-fold higher than those of corresponding unsubstituted matched pairs and can be rationalized from increased hydrophobic interactions with the FimH hydrophobic ridge (Ile13) or "tyrosine gate" (Tyr137 and Tyr48) also lined by Ile52. The lead mannosides have increased metabolic stability and oral bioavailability as determined from in vitro PAMPA predictive model of cellular permeability and in vivo pharmacokinetic studies in mice, thereby representing advanced preclinical candidates with promising potential as novel therapeutics for the clinical treatment and prevention of recurring urinary tract infections.