methyl 4,6-diazido-2,3-di-O-benzyl-4,6-dideoxy-α-D-glucopyranoside | 674782-48-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 4,6-diazido-2,3-di-O-benzyl-4,6-dideoxy-α-D-glucopyranoside
• CAS: 674782-48-0
• 化学式: C₂₁H₂₄N₆O₄
• 分子量: 424.459
• InChiKey: YOILIINVCANQPF-ADAARDCZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.52
• 重原子数：
  31.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  134.44
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl 4,6-diazido-2,3-di-O-benzyl-4,6-dideoxy-α-D-glucopyranoside 在 硫酸 、 乙酸肼 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 4,6-diazido-2,3-di-O-acetyl-4,6-dideoxy-α-D-glucopyranosyl trichloroacetimidate
  参考文献：
  名称：

  Application of the Synthetic Aminosugars for Glycodiversification:  Synthesis and Antimicrobial Studies of Pyranmycin

  摘要：

  A divergent approach was employed for the synthesis of aminosugars, from which a novel library of aminoglycoside antibiotics (pyranmycins) was synthesized. Pyranmycins have comparable antibacterial activity as neomycin, a clinically used aminoglycoside antibiotic, against Escherichia coli, Staphylococcus aureus, Bacillus subtilis, and Mycobacterium smegmatis. In addition, pyranmycins, like streptomycin, are bacteriocidal while isoniazid (INH) is bacteriostatic. Therefore, pyranmycins may provide new therapeutic options in the treatment against tuberculosis. Several members of pyranmycins also manifest modest anti-Tat and anti-Rev activities, which may aid in the development of new anti-HIV agents. Although the antibacterial activity of pyranmycins against aminoglycoside resistant bacteria is less than expected, the synthetic methodologies of utilizing a library of aminosugars can be a model for future studies of glycodiversification or glycorandomization.

  DOI：

  10.1021/jo035290r
• 作为产物：
  描述：

  methyl 2,3-O-dibenzyl-4,6-O-benzylidene-α-D-glucopyranoside 在 吡啶 、 sodium tetrahydroborate 、 sodium azide 、 草酰氯 、 三氟甲磺酸酐 、 对甲苯磺酸 、 二甲基亚砜 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 methyl 4,6-diazido-2,3-di-O-benzyl-4,6-dideoxy-α-D-glucopyranoside
  参考文献：
  名称：

  Application of the Synthetic Aminosugars for Glycodiversification:  Synthesis and Antimicrobial Studies of Pyranmycin

  摘要：

  A divergent approach was employed for the synthesis of aminosugars, from which a novel library of aminoglycoside antibiotics (pyranmycins) was synthesized. Pyranmycins have comparable antibacterial activity as neomycin, a clinically used aminoglycoside antibiotic, against Escherichia coli, Staphylococcus aureus, Bacillus subtilis, and Mycobacterium smegmatis. In addition, pyranmycins, like streptomycin, are bacteriocidal while isoniazid (INH) is bacteriostatic. Therefore, pyranmycins may provide new therapeutic options in the treatment against tuberculosis. Several members of pyranmycins also manifest modest anti-Tat and anti-Rev activities, which may aid in the development of new anti-HIV agents. Although the antibacterial activity of pyranmycins against aminoglycoside resistant bacteria is less than expected, the synthetic methodologies of utilizing a library of aminosugars can be a model for future studies of glycodiversification or glycorandomization.

  DOI：

  10.1021/jo035290r

文献信息

• Preparation of Primary and Secondary Azidosugars from Diols using the Dioxaphosphorane Methodology
  作者：Dominique Lafont、Paul Boullanger

  DOI：10.1080/07328309908544029

  日期：1999.1

  Treatment of methyl 2,3-di-O-benzyl-alpha-D-glucopyranoside (1), methyl 2,3-di-O-acetyl-alpha-D-glucopyranoside (4), 3-O-benzyl-1,2-O-(1-methylethylidene)-alpha-D-glucofuranose (6), 3-O-acetyl-1,2-O-(1-methylethylidene)-alpha-D-glucofuranose (9), 1,2-O-(1-methylethylidene)-alpha-D-xylofuranose (11) and methyl 2,3-di-O-acetyl-alpha-D-galactopyranoside (15) with diisopropylazodicarboxylate-triphenylphosphine in tetrahydrofuran led to the corresponding dioxaphosphoranes, which were opened by trimethylsilyl azide affording the silylated primary azidodeoxysugars. When the same reaction was performed on methyl 2,3-di-O-benzyl-alpha-D-galactopyranoside (20), an inversion of the regioselectivity of the dioxaphosphorane opening was observed, leading mainly to the 4-azido-4-deoxy-alpha-D-glucopyranoside derivative 27.