2,5-anhydro-1-azido-1-deoxy-D-mannitol | 243469-61-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,5-anhydro-1-azido-1-deoxy-D-mannitol
• 英文别名: (2R,3S,4S,5R)-2-(azidomethyl)-5-(hydroxymethyl)oxolane-3,4-diol
• CAS: 243469-61-6
• 化学式: C₆H₁₁N₃O₄
• 分子量: 189.171
• InChiKey: SXQJFSPBUVMKMT-KVTDHHQDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  84.3
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,5-anhydro-1-azido-1-deoxy-D-mannitol 在 palladium on activated charcoal 咪唑 、 六甲基磷酰三胺 、 正丁基锂 、 氢气 、 碘 、 三苯基膦 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 37.0h， 生成 (2R,3S,4S,5R)-2-((bis(cyclohexylmethyl)amino)methyl)-5-(2-((2R,3S,4S,5R)-5-((bis(cyclohexylmethyl)amino)methyl)-3,4-dihydroxy-tetrahydrofuran-2-yl)ethyl)-tetrahydrofuran-3,4-diol
  参考文献：
  名称：

  Synthesis of symmetrical C- and pseudo-symmetrical O-linked disaccharide analogs for arabinosyltransferase inhibitory activity in Mycobacterium tuberculosis

  摘要：

  Herein we report the Synthesis of symmetrical C-linked and pseudo-symmetrical O-linked disaccharides structurally related to Araf motifs present in the cell wall of MTB. Their activity in a competition-based arabinosyltransferase assay using [C-14]-DPA as the glycosyl donor is also presented. In addition, in vitro inhibitory activity for the disaccharides was determined in a colorimetric broth microdilution assay system against MTB H37Ra and Mycobacterium avium. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.05.099
• 作为产物：
  描述：

  2,5-脱水-D-甘露醇 在 sodium azide 作用下， 以 吡啶 、 N,N-二甲基甲酰胺 为溶剂， 反应 42.0h， 生成 2,5-anhydro-1-azido-1-deoxy-D-mannitol
  参考文献：
  名称：

  Ethambutol–sugar hybrids as potential inhibitors of mycobacterial cell-wall biosynthesis

  摘要：

  Ethambutol is an established front-line agent for the treatment of tuberculosis, and is also active against Mycobacterium avium infection. However, this agent exhibits toxicity, and is considered to have low potency. The action of ethambutol on the mycobacterial cell wall, particularly the arabinan, and comparison of the structure of ethambutol with several of the cell-wall saccharides, suggested that ethambutol-saccharide hybrids might lead to agents with a more selective mechanism of action. To this end, eight ethambutol-saccharide hybrids were synthesized and screened against M. tuberculosis and several clinical isolates of M. avium. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00069-5

文献信息

• Ethambutol–sugar hybrids as potential inhibitors of mycobacterial cell-wall biosynthesis
  作者：Robert C Reynolds、Namita Bansal、Jerry Rose、Joyce Friedrich、William J Suling、Joseph A Maddry

  DOI：10.1016/s0008-6215(99)00069-5

  日期：1999.4

  Ethambutol is an established front-line agent for the treatment of tuberculosis, and is also active against Mycobacterium avium infection. However, this agent exhibits toxicity, and is considered to have low potency. The action of ethambutol on the mycobacterial cell wall, particularly the arabinan, and comparison of the structure of ethambutol with several of the cell-wall saccharides, suggested that ethambutol-saccharide hybrids might lead to agents with a more selective mechanism of action. To this end, eight ethambutol-saccharide hybrids were synthesized and screened against M. tuberculosis and several clinical isolates of M. avium. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Synthesis and Application of Carbohydrate-Derived Morpholine Amino Acids
  作者：Gijsbert M. Grotenbreg、Alphert E. Christina、Annelies E. M. Buizert、Gijsbert A. van der Marel、Herman S. Overkleeft、Mark Overhand

  DOI：10.1021/jo048630x

  日期：2004.11.1

  The synthesis of series of diversely functionalized epsilon-morpholine amino acids (MAAs, 5a-h) starting from an E-sugar amino acid and following a two-step oxidative glycol cleavage/reductive amination strategy, is described. In an alternative synthetic scheme, diastereoisomerically pure delta-MAAs (12a,b) were obtained. Oligopeptides containing MAAs were prepared either by direct incorporation of a MAA building block or by subjecting a fully assembled SAA-containing peptide to the two-step glycol cleavage/reductive amination procedure.
• Synthesis of symmetrical C- and pseudo-symmetrical O-linked disaccharide analogs for arabinosyltransferase inhibitory activity in Mycobacterium tuberculosis
  作者：Ashish K. Pathak、Vibha Pathak、James R. Riordan、William J. Suling、Sudagar S. Gurcha、Gurdyal S. Besra、Robert C. Reynolds

  DOI：10.1016/j.bmcl.2007.05.099

  日期：2007.8

  Herein we report the Synthesis of symmetrical C-linked and pseudo-symmetrical O-linked disaccharides structurally related to Araf motifs present in the cell wall of MTB. Their activity in a competition-based arabinosyltransferase assay using [C-14]-DPA as the glycosyl donor is also presented. In addition, in vitro inhibitory activity for the disaccharides was determined in a colorimetric broth microdilution assay system against MTB H37Ra and Mycobacterium avium. (c) 2007 Elsevier Ltd. All rights reserved.