phenyl 3-azido-4,6-O-benzylidene-3-deoxy-1-thio-β-D-glucopyranoside | 868258-56-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 3-azido-4,6-O-benzylidene-3-deoxy-1-thio-β-D-glucopyranoside
• 英文别名: (2R,4aR,6S,7R,8R,8aS)-8-azido-2-phenyl-6-phenylsulfanyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-ol
• CAS: 868258-56-4
• 化学式: C₁₉H₁₉N₃O₄S
• 分子量: 385.444
• InChiKey: WQRHBXGAEHEKBE-UPGMHYFXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  87.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  phenyl 3-azido-4,6-O-benzylidene-3-deoxy-1-thio-β-D-glucopyranoside 在 吡啶 、 三氯化铝 、 硼烷-三甲胺络合物 、 四丁基碘化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 phenyl 4-O-acetyl-3-azido-2,6-di-O-benzyl-3-deoxy-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  Glycodiversification for the Optimization of the Kanamycin Class Aminoglycosides

  摘要：

  In an effort to optimize the antibacterial activity of kanamycin class aminoglycoside antibiotics, we have accomplished the synthesis and antibacterial assay of new kanamycin B analogues. A rationale-based glycodiversification strategy was employed. The activity of the lead is comparable to that of commercially available kanamycin. These new members, however, were found to be inactive against aminoglycoside resistant bacteria. Molecular modeling was used to provide the explanation. Thus, a new strategy for structural modifications of kanamycin class aminoglycosides is suggested.

  DOI：

  10.1021/jm050368c
• 作为产物：
  描述：

  3-azido-1,3-dideoxy-1-(phenylsulfenyl)-2,4,6-tri-O-acetyl-β-D-gluco-pyranose 在 sodium methylate 、 对甲苯磺酸 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 phenyl 3-azido-4,6-O-benzylidene-3-deoxy-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Glycodiversification for the Optimization of the Kanamycin Class Aminoglycosides

  摘要：

  In an effort to optimize the antibacterial activity of kanamycin class aminoglycoside antibiotics, we have accomplished the synthesis and antibacterial assay of new kanamycin B analogues. A rationale-based glycodiversification strategy was employed. The activity of the lead is comparable to that of commercially available kanamycin. These new members, however, were found to be inactive against aminoglycoside resistant bacteria. Molecular modeling was used to provide the explanation. Thus, a new strategy for structural modifications of kanamycin class aminoglycosides is suggested.

  DOI：

  10.1021/jm050368c

文献信息

• Synthesis of the tetrasaccharide repeating unit of the O-antigen from Pseudomonas putida BIM B-1100 having rare D-Quip3NAc
  作者：Madhumita Bera、Balaram Mukhopadhyay

  DOI：10.1016/j.carres.2020.107955

  日期：2020.3

  Chemical synthesis of the complex tetrasaccharide repeating unit of the O-antigen from Pseudomonas putida BIM B-1100 is accomplished in the form of its 2-aminoethyl glycoside to leave the scope for further glycoconjugate formation without hampering the anomeric stereochemistry. A [2 + 2] strategy is followed to complete the total synthesis and a late stage TEMPO mediated oxidation is used to install

  来自恶臭假单胞菌BIM B-1100的O抗原的复杂四糖重复单元的化学合成以其2-氨基乙基糖苷的形式完成，从而为进一步的糖缀合物形成提供了范围，而不会妨碍异头异构体的立体化学。遵循[2 + 2]策略以完成总合成，并使用后期TEMPO介导的氧化来安装所需的糖醛酸。自由基介导的6-脱氧和随后的保护基操纵策略用于从合适的d-葡萄糖胺衍生物制备稀有的D-FucpNAc和D-Quip3NAc衍生物。
• Chemical synthesis of the rare D-Fuc3NAc containing tetrasaccharide repeating unit of the O-antigenic polysaccharide from E. coli O74
  作者：Anirban Bera、Balaram Mukhopadhyay

  DOI：10.1016/j.carres.2021.108366

  日期：2021.8

  Chemical synthesis of the tetrasaccharide repeating unit of the O-antigen from E. coli O74 is accomplished by a convergent [2 + 2] block synthesis strategy. The challenging rare D-Fuc3NAc has been prepared using DTBP and TIPST mediated deoxygenation reaction. Other monosaccharide synthons are prepared through rational protecting group manipulations and the stereoselective glycosylations are achieved

  来自大肠杆菌O74 的O抗原的四糖重复单元的化学合成是通过收敛的 [2 + 2] 嵌段合成策略来完成的。使用 DTBP 和 TIPST 介导的脱氧反应制备了具有挑战性的稀有 D-Fuc3NAc。其他单糖合成子是通过合理的保护基操作制备的，并且立体选择性糖基化是通过硫代糖苷或糖基三氯乙酰亚胺酯的活化来实现的。目标四糖以其 2-氨基乙基糖苷的形式制成，以促进进一步糖缀合物的形成，而不影响异头立体化学。
• Biological evaluation of carbohydrate-based aprepitant analogs for neuroblastoma treatment
  作者：Victoria Valdivia、Rocío Recio、Patricia Lerena、Esther Pozo、Rosario Serrano、Raúl Calero、Cristina Pintado、Manuel Pernia Leal、Nazaret Moreno-Rodríguez、Juan Ángel Organero、Noureddine Khiar、Inmaculada Fernández

  DOI：10.1016/j.ejmech.2023.116021

  日期：2024.1

  affinity and NK1R antagonistic activity with a broad-spectrum anticancer activity and an important selectivity. In this new study, we explore the selective cytotoxic effects of these derivatives for the treatment of NB. Furthermore, we describe the design and stereoselective synthesis of a new generation of d-glucose derivatives as Aprepitant analogs, supported by docking studies. This approach showed that

  使用阿瑞吡坦（目前用作治疗化疗相关恶心和呕吐的临床药物）的 NK1R 拮抗剂的不同研究表明，NK1R 的药理抑制可有效减少神经母细胞瘤 (NB) 等多种肿瘤类型的生长。在之前的工作中，我们证明了一系列基于碳水化合物的阿瑞吡坦类似物，衍生自d-半乳糖或l-阿拉伯糖，具有高亲和力和NK1R拮抗活性，具有广谱抗癌活性和重要的选择性。在这项新研究中，我们探索了这些衍生物治疗 NB 的选择性细胞毒性作用。此外，我们描述了新一代d-葡萄糖衍生物（阿瑞吡坦类似物）的设计和立体选择性合成，并得到对接研究的支持。这种方法表明，我们大多数基于碳水化合物的类似物的选择性明显高于阿瑞匹坦。半乳糖基衍生物2α已在体外表现出显着的针对NB 的选择性细胞毒活性，其IC 50值与Aprepitant 及其前药Fosaprepitant 的范围相同。有趣的是，衍生物2α表现出与阿瑞匹坦类似的细胞凋亡作用。 此外，我们可以选
• Structure–Activity Relationships for Antibacterial to Antifungal Conversion of Kanamycin to Amphiphilic Analogues
  作者：Marina Fosso、Madher N. AlFindee、Qian Zhang、Vincent de Paul Nzuwah Nziko、Yukie Kawasaki、Sanjib K. Shrestha、Jeremiah Bearss、Rylee Gregory、Jon Y. Takemoto、Cheng-Wei Tom Chang

  DOI：10.1021/acs.joc.5b00248

  日期：2015.5.1

  Novel fungicides are urgently needed. It was recently reported that the attachment of an octyl group at the O-4 '' position of kanamycin B converts this antibacterial aminoglycoside into a novel antifungal agent. To elucidate the structure-activity relationship (SAR) for this phenomenon, a lead compound FG03 with a hydroxyl group replacing the 3 ''-NH2 group of kanamycin B was synthesized. FG03's antifungal activity and Synthetic scheme inspired the synthesis of a library of kanamycin B analogues alkylated at various hydroxyl groups. SAR. studies of the library revealed that for antifungal activity the O-4 '' position is the optimal site for attaching a linear alkyl chain and that the 3 ''-NH2 and 6 ''-OH groups of the kanamycin B parent molecule are not essential for antifungal activity. The discovery of lead compound, FG03, is an example of reviving clinically obsolete drugs like kanamycin by simple chemical modification and an alternative strategy for discovering novel antimicrobials.
• Glycodiversification for the Optimization of the Kanamycin Class Aminoglycosides
  作者：Jinhua Wang、Jie Li、Hsiao-Nung Chen、Huiwen Chang、Christabel Tomla Tanifum、Hsiu-Hsiang Liu、Przemyslaw G. Czyryca、Cheng-Wei Tom Chang

  DOI：10.1021/jm050368c

  日期：2005.10.1

  In an effort to optimize the antibacterial activity of kanamycin class aminoglycoside antibiotics, we have accomplished the synthesis and antibacterial assay of new kanamycin B analogues. A rationale-based glycodiversification strategy was employed. The activity of the lead is comparable to that of commercially available kanamycin. These new members, however, were found to be inactive against aminoglycoside resistant bacteria. Molecular modeling was used to provide the explanation. Thus, a new strategy for structural modifications of kanamycin class aminoglycosides is suggested.