Methyl-6-chlor-6-deoxy-α-D-mannopyranosid | 4990-80-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methyl-6-chlor-6-deoxy-α-D-mannopyranosid
• 英文别名: 6-Chlor-methyl-α-D-mannopyranosid；(2S,3S,4S,5S,6S)-2-(chloromethyl)-6-methoxyoxane-3,4,5-triol
• CAS: 4990-80-1
• 化学式: C₇H₁₃ClO₅
• 分子量: 212.63
• InChiKey: TZECRHYTLKLTSH-VEIUFWFVSA-N

物化性质

• 沸点：
  370.4±42.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  79.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Methyl-6-chlor-6-deoxy-α-D-mannopyranosid 在 sodium tetrahydroborate 、 sodium azide 、 palladium on activated charcoal 、 氢气 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.0h， 生成 (2R,3S,4S,5S,6S)-2-((benzylamino)methyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol
  参考文献：
  名称：

  Discovery of Two Classes of Potent Glycomimetic Inhibitors of Pseudomonas aeruginosa LecB with Distinct Binding Modes

  摘要：

  The treatment of infections due to the opportunistic pathogen Pseudomonas aeruginosa is often difficult, as a consequence of bacterial biofilm formation. Such a protective environment shields the bacterium from host defense and antibiotic treatment and secures its survival. One crucial factor for maintenance of the biofilm architecture is the carbohydrate-binding lectin LecB. Here, we report the identification of potent mannose-based LecB inhibitors from a screening of four series of mannosides in a novel competitive binding assay for LecB. Cinnamide and sulfonamide derivatives are inhibitors of bacterial adhesion with up to a 20-fold increase in affinity to LecB compared to the natural ligand methyl mannoside. Because many lectins of the host require terminal saccharides (e.g., fucosides), such capped structures as reported here may offer a beneficial selectivity profile for the pathogenic lectin. Both classes of compounds show distinct binding modes at the protein, offering the advantage of a simultaneous development of two new lead structures as anti-pseudomonadal drugs with an anti-virulence mode of action.

  DOI：

  10.1021/cb400371r
• 作为产物：
  描述：

  甲基-D-丙噻 在 偶氮二甲酸二异丙酯 、 三苯基膦 、 三甲基氯硅烷 作用下， 以 甲苯 为溶剂， 反应 3.25h， 生成 Methyl-6-chlor-6-deoxy-α-D-mannopyranosid
  参考文献：
  名称：

  通过Mitsunobu反应 在碳水化合物和非糖醇中进行区域选择性一氯取代：在合成瑞波西汀中的应用†

  摘要：

  据报道通过Mitsunobu反应的区域选择性高产一氯取代（氯醇形成）。在碳水化合物和受阻位的非糖中，仅伯羟基被氯化，而在非糖1,2-和1,3-醇中，主要发生仲氯取代。与常规的Mitsunobu反应可逆生成环氧化物的方法不同，通用的方法可在保留结构的情况下间接获得环氧化物。该方法已成功用作抗抑郁药光学活性非对映异构体合成的关键步骤瑞波西汀（R）-2，3- O-环己叉基-D-甘油醛的总产率为〜43％。

  DOI：

  10.1039/c3ob40853a

文献信息

• Two Reagent Systems for Converting Hydroxy Compounds into Chlorides using the Triphenylphosphine/Imidazole System
  作者：Per J. Garegg、Rolf Johansson、Bertil Samuelsson

  DOI：10.1055/s-1984-30769

  日期：——
• US4225590A
  申请人：——

  公开号：US4225590A

  公开（公告）日：1980-09-30
• Regioselective monochloro substitution in carbohydrates and non-sugar alcohols via Mitsunobu reaction: applications in the synthesis of reboxetine
  作者：Abdul Rouf Dar、Mushtaq A. Aga、Brijesh Kumar、Syed Khalid Yousuf、Subhash Chandra Taneja

  DOI：10.1039/c3ob40853a

  日期：——

  A regioselective high yielding monochloro substitution (chlorohydrin formation) via Mitsunobu reaction is reported. In carbohydrates and sterically hindered non-sugars, only the primary hydroxyl group is chlorinated, whereas in the non-sugar 1,2- and 1,3-alcohols, predominantly the secondary chloride substitution occurs. The versatile methodology provides indirect access to epoxides with the retention

  据报道通过Mitsunobu反应的区域选择性高产一氯取代（氯醇形成）。在碳水化合物和受阻位的非糖中，仅伯羟基被氯化，而在非糖1,2-和1,3-醇中，主要发生仲氯取代。与常规的Mitsunobu反应可逆生成环氧化物的方法不同，通用的方法可在保留结构的情况下间接获得环氧化物。该方法已成功用作抗抑郁药光学活性非对映异构体合成的关键步骤瑞波西汀（R）-2，3- O-环己叉基-D-甘油醛的总产率为〜43％。
• Discovery of Two Classes of Potent Glycomimetic Inhibitors of <i>Pseudomonas aeruginosa</i> LecB with Distinct Binding Modes
  作者：Dirk Hauck、Ines Joachim、Benjamin Frommeyer、Annabelle Varrot、Bodo Philipp、Heiko M. Möller、Anne Imberty、Thomas E. Exner、Alexander Titz

  DOI：10.1021/cb400371r

  日期：2013.8.16

  The treatment of infections due to the opportunistic pathogen Pseudomonas aeruginosa is often difficult, as a consequence of bacterial biofilm formation. Such a protective environment shields the bacterium from host defense and antibiotic treatment and secures its survival. One crucial factor for maintenance of the biofilm architecture is the carbohydrate-binding lectin LecB. Here, we report the identification of potent mannose-based LecB inhibitors from a screening of four series of mannosides in a novel competitive binding assay for LecB. Cinnamide and sulfonamide derivatives are inhibitors of bacterial adhesion with up to a 20-fold increase in affinity to LecB compared to the natural ligand methyl mannoside. Because many lectins of the host require terminal saccharides (e.g., fucosides), such capped structures as reported here may offer a beneficial selectivity profile for the pathogenic lectin. Both classes of compounds show distinct binding modes at the protein, offering the advantage of a simultaneous development of two new lead structures as anti-pseudomonadal drugs with an anti-virulence mode of action.