6-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-1,3,2',6'-tetraazidoneamine | 671809-33-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-1,3,2',6'-tetraazidoneamine
• 英文别名: (2R,3S,4R,5R,6R)-5-azido-2-(azidomethyl)-6-[(1R,2S,3S,4R,6S)-4,6-diazido-2-hydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxycyclohexyl]oxyoxane-3,4-diol
• CAS: 671809-33-9
• 化学式: C₄₆H₅₂N₁₂O₁₁
• 分子量: 948.993
• InChiKey: MVALXYOWCIYGCE-IXGGUPDISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  69
• 可旋转键数：
  22
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  192
• 氢给体数：
  3
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  6-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-1,3,2',6'-tetraazidoneamine 在 palladium dihydroxide 氢气 作用下， 以 乙醇 、 氯仿 、 水 为溶剂， 20.0 ℃ 、344.74 kPa 条件下， 以63%的产率得到6-O-(α-D-galactopyranosyl)neamine
  参考文献：
  名称：

  Regioselective Glycosylation of Neamine Core:  A Facile Entry to Kanamycin B Related Analogues

  摘要：

  Introduction of a sugar unit at either the O5 or O6 position of various neamine derivatives in excellent selectivity and yields is described here. Application to the synthesis of kanamycin analogues is also highlighted.

  DOI：

  10.1021/ol0363927
• 作为产物：
  描述：

  Acetic acid (2R,3R,4R,5R,6R)-3-acetoxy-5-azido-2-azidomethyl-6-[(1R,2S,3S,4R,6S)-4,6-diazido-2-hydroxy-3-((2S,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-tetrahydro-pyran-4-yl ester 在 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 生成 6-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-1,3,2',6'-tetraazidoneamine
  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