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

中文名称
——
中文别名
——
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
6-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-1,3,2',6'-tetraazidoneamine化学式
CAS
671809-33-9
化学式
C46H52N12O11
mdl
——
分子量
948.993
InChiKey
MVALXYOWCIYGCE-IXGGUPDISA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

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

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量

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'-tetraazidoneaminepalladium dihydroxide 氢气 作用下, 以 乙醇氯仿 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
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