phenyl 2-O-benzyl-6-deoxy-1-thio-β-D-allopyranoside | 868258-62-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 2-O-benzyl-6-deoxy-1-thio-β-D-allopyranoside
• 英文别名: (2R,3S,4R,5R,6S)-2-methyl-5-phenylmethoxy-6-phenylsulfanyloxane-3,4-diol
• CAS: 868258-62-2
• 化学式: C₁₉H₂₂O₄S
• 分子量: 346.447
• InChiKey: DXFZSIVVKMWYFP-PYJZQUQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  84.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  phenyl 2-O-benzyl-6-deoxy-1-thio-β-D-allopyranoside 在 palladium dihydroxide 4-二甲氨基吡啶 、 sodium hydroxide 、 N-碘代丁二酰亚胺 、 sodium azide 、 氢气 、 sodium methylate 、 溶剂黄146 、 N,N-二异丙基乙胺 、 三甲基膦 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 33.0h， 生成 6''-deoxykanamycin B
  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：

  phenyl 3,4-di-O-acetyl-2-O-benzyl-6-deoxy-1-thio-β-D-allopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以90%的产率得到phenyl 2-O-benzyl-6-deoxy-1-thio-β-D-allopyranoside
  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

• Direct Synthesis of 2-Deoxy-β-Glycosides via Anomeric <i>O</i>-Alkylation with Secondary Electrophiles
  作者：Danyang Zhu、Kedar N. Baryal、Surya Adhikari、Jianglong Zhu

  DOI：10.1021/ja4116956

  日期：2014.2.26

  An approach for direct synthesis of biologically significant 2-deoxy-beta-glycosides has been developed via O-alkylation of a variety of 2-deoxy-sugar-derived anomeric alkoxides using challenging secondary triflates as electrophiles. It was found a free hydroxyl group at C3 of the 2-deoxy-sugar-derived lactols is required in order to achieve synthetically efficient yields. This method has also been applied to the convergent synthesis of a 2-deoxy-beta-tetrasaccharide.
• 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.