methyl 4-azido-2,3-di-O-benzyl-4,6-dideoxy-α-D-galactopyranoside | 14532-80-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4-azido-2,3-di-O-benzyl-4,6-dideoxy-α-D-galactopyranoside
• 英文别名: 4-Azido-4,6-didesoxy-2,3-di-O-benzyl-methyl-α-D-galaktopyranosid；(2S,3R,4S,5S,6R)-5-azido-2-methoxy-6-methyl-3,4-bis(phenylmethoxy)oxane
• CAS: 14532-80-0
• 化学式: C₂₁H₂₅N₃O₄
• 分子量: 383.447
• InChiKey: NSZAJKYIEURLSO-JUHPOPGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  51.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 4-azido-2,3-di-O-benzyl-4,6-dideoxy-α-D-galactopyranoside 在 sodium tetrahydroborate 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 8.0h， 生成 ((2R,3S,4S,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-2-methyl-tetrahydro-pyran-3-yl)-methyl-amine
  参考文献：
  名称：

  Convenient Procedure for One-pot Conversion of Azides to N-Monomethylamines

  摘要：

  介绍了叠氮化物与 N-单甲基胺的单锅转化。已开发出两种可选方案，它们共享第一阶段，即叠氮化物与 (CH3)3P 反应生成相应的亚氨基磷烷。由此生成的施陶丁格中间体可以用 CH3I 进行甲基化并水解（方法 A），或者用 (HCHO) n 处理并用 NaBH4 还原（方法 B），从而以高产率得到相应的 N-单甲胺。

  DOI：

  10.1055/s-2001-14646
• 作为产物：
  描述：

  4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside 在 吡啶 、 lithium aluminium tetrahydride 、 三氟甲磺酸酐 、 四丁基碘化铵 、 sodium hydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 methyl 4-azido-2,3-di-O-benzyl-4,6-dideoxy-α-D-galactopyranoside
  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

• Application of the Synthetic Aminosugars for Glycodiversification:  Synthesis and Antimicrobial Studies of Pyranmycin
  作者：Bryan Elchert、Jie Li、Jinhua Wang、Yu Hui、Ravi Rai、Roger Ptak、Priscilla Ward、Jon Y. Takemoto、Mekki Bensaci、Cheng-Wei Tom Chang

  DOI：10.1021/jo035290r

  日期：2004.3.1

  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.
• Convenient Procedure for One-pot Conversion of Azides to N-Monomethylamines
  作者：Hirohisa Kato、Ken Ohmori、Keisuke Suzuki

  DOI：10.1055/s-2001-14646

  日期：——

  One-pot conversion of azides to N-monomethylamines is described. Two optional protocols have been developed, which share the first stage, the reaction of an azide with (CH3)3P to generate the corresponding iminophosphorane. This Staudinger intermediate, thus generated, is either methylated with CH3I and hydrolyzed (method A), or treated with (HCHO) n and reduced with NaBH4 (method B), thereby giving the corresponding N-monomethylamine in high yield.

  介绍了叠氮化物与 N-单甲基胺的单锅转化。已开发出两种可选方案，它们共享第一阶段，即叠氮化物与 (CH3)3P 反应生成相应的亚氨基磷烷。由此生成的施陶丁格中间体可以用 CH3I 进行甲基化并水解（方法 A），或者用 (HCHO) n 处理并用 NaBH4 还原（方法 B），从而以高产率得到相应的 N-单甲胺。