phenyl 2,3-di-O-benzyl-6-deoxy-4-O-((R)-glycidyl)-1-thio-β-D-glucopyranoside | 868258-83-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 2,3-di-O-benzyl-6-deoxy-4-O-((R)-glycidyl)-1-thio-β-D-glucopyranoside
• 英文别名: (2R,3R,4S,5R,6S)-2-methyl-3-[[(2R)-oxiran-2-yl]methoxy]-4,5-bis(phenylmethoxy)-6-phenylsulfanyloxane
• CAS: 868258-83-7
• 化学式: C₂₉H₃₂O₅S
• 分子量: 492.636
• InChiKey: MSACEPTUQPNMKF-RTCJPIHJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  74.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  phenyl 2,3-di-O-benzyl-6-deoxy-4-O-((R)-glycidyl)-1-thio-β-D-glucopyranoside 在 吡啶 、 cerium(III) chloride 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 24.5h， 生成 Trifluoro-methanesulfonic acid (R)-1-azidomethyl-2-((2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-3-yloxy)-ethyl ester
  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：

  (R)-对甲苯磺酸缩水甘油酯 、 phenyl 2,3-di-O-benzyl-6-deoxy-1-thio-β-D-glucopyranoside 在 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以86%的产率得到phenyl 2,3-di-O-benzyl-6-deoxy-4-O-((R)-glycidyl)-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

• 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.