isoamyl-6-O-trimethylacetyl-2,3-dideoxy-α-D-glycero-hex-2-enopyranosid-4-ulose | 1310542-94-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: isoamyl-6-O-trimethylacetyl-2,3-dideoxy-α-D-glycero-hex-2-enopyranosid-4-ulose
• 英文别名: [(2S,6R)-2-isopentyloxy-5-oxo-2H-pyran-6-yl]methyl 2,2-dimethylpropanoate；[(2S,6R)-2-(3-methylbutoxy)-5-oxo-2H-pyran-6-yl]methyl 2,2-dimethylpropanoate
• CAS: 1310542-94-9
• 化学式: C₁₆H₂₆O₅
• 分子量: 298.379
• InChiKey: CYLQSHHTLUSPSS-KGLIPLIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  isoamyl-6-O-trimethylacetyl-2,3-dideoxy-α-D-glycero-hex-2-enopyranosid-4-ulose 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 1.33h， 以88%的产率得到[(2R,6S)-6-(3-methylbutoxy)-3-oxooxan-2-yl]methyl 2,2-dimethylpropanoate
  参考文献：
  名称：

  2,3-Dideoxy hex-2-enopyranosid-4-uloses as promising new anti-tubercular agents: Design, synthesis, biological evaluation and SAR studies

  摘要：

  The alarming resurgence of tuberculosis (TB) underlines the urgent need for development of new and potent anti-TB drugs. Towards this goal we herein report the design and synthesis of 2,3-dideoxy hex-2-enopyranosid-4-uloses as promising new anti-tubercular agents. These easily accessible, small molecules were found to exhibit in vitro activity against Mycobacterium tuberculosis H37Rv in a MIC range of 0.78 mu g/mL to 25 mu g/mL. A detailed SAR study on these hex-2-enopyranosid-4-uloses led to the identification of compound 5g (5007-724) which on the basis of low MIC (0.78 mu g/mL-M. tuberculosis H37Rv; 1.56 mu g/mL-MDR, SDR strains of M. tuberculosis; 0.78 mu g/mL-inhibition of intracellular replication of M. tuberculosis) and SI value of 13.5 has been identified as a promising lead molecule. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.03.002
• 作为产物：
  描述：

  (2R,3S,6S)-2-(hydroxymethyl)-6-isopentyloxy-3,6-dihydro-2H-pyran-3-ol 在 吡啶 、 manganese(IV) oxide 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 52.0h， 生成 isoamyl-6-O-trimethylacetyl-2,3-dideoxy-α-D-glycero-hex-2-enopyranosid-4-ulose
  参考文献：
  名称：

  2,3-Dideoxy hex-2-enopyranosid-4-uloses as promising new anti-tubercular agents: Design, synthesis, biological evaluation and SAR studies

  摘要：

  The alarming resurgence of tuberculosis (TB) underlines the urgent need for development of new and potent anti-TB drugs. Towards this goal we herein report the design and synthesis of 2,3-dideoxy hex-2-enopyranosid-4-uloses as promising new anti-tubercular agents. These easily accessible, small molecules were found to exhibit in vitro activity against Mycobacterium tuberculosis H37Rv in a MIC range of 0.78 mu g/mL to 25 mu g/mL. A detailed SAR study on these hex-2-enopyranosid-4-uloses led to the identification of compound 5g (5007-724) which on the basis of low MIC (0.78 mu g/mL-M. tuberculosis H37Rv; 1.56 mu g/mL-MDR, SDR strains of M. tuberculosis; 0.78 mu g/mL-inhibition of intracellular replication of M. tuberculosis) and SI value of 13.5 has been identified as a promising lead molecule. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.03.002

文献信息

• Chiral Pyridin-3-ones and Pyridines: Syntheses of Enantiopure 2,4-Disubstituted 6-Hydroxy-1,6-Dihydro-<i>2H</i>-Pyridin-3-ones, 2,3-Disubstituted 4-Iodopyridines, and Enantiopure 2,3-Disubstituted 4-Pyridinemethanols
  作者：Irfan Husain、Mohammad Saquib、Vikas Bajpai、Brijesh Kumar、Arun K. Shaw

  DOI：10.1021/jo201662n

  日期：2011.11.4

  azide derivatives, transfer of chiral aryl/alkyl methanols from enulosides to pyridin-3-ones and pyridines, high yields, and short reaction times are key features of this method. The utility of the method has been further exemplified by demonstrating the usage of the 2-substituted 3-acetoxy-4-iodopyridine for the construction of biologically significant molecules like 2,7-disubstituted furo[2,3-c]pyridines

  已经描述了开发一种创新方法的方法，该方法从d-葡糖开始通过氮杂-Achmatowicz转化获得对映体纯的2,4-二取代的6-羟基-1,6-二氢-2 H-吡啶-3-酮。这些高度官能化的吡啶-3-酮已用于通过快速有效的Et 3 N / Ac 2合成连续取代的吡啶O促进了环消除，芳构化级联反应，使重要的吡啶基结构单元（如2-取代的3-乙酰氧基-4-碘吡啶和对映纯的2-取代的3-乙酰氧基-4-吡啶甲醇具有苄基立体生成中心，易于合成）易于组装否则会很乏味。使用市售糖作为原料，温和的反应条件，α-糠基叠氮化物衍生物的催化转移氢（CTH），手性芳基/烷基甲醇从烯醇类转移至吡啶3-酮和吡啶的方法，收率高，反应时间短反应时间是该方法的关键特征。通过证明2-取代的3-乙酰氧基-4-碘吡啶用于构建生物学上重要的分子（例如2,7-二取代的呋喃[2,3-]）的方法，该方法的实用性得到了进一步的例证。Ç ]吡啶和7,7'