methyl 6-O-trimethylacetyl-2,3-dideoxy-α-D-glycero-hex-2-enopyranosid-4-ulose | 1174211-71-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: methyl 6-O-trimethylacetyl-2,3-dideoxy-α-D-glycero-hex-2-enopyranosid-4-ulose
• 英文别名: [(2S,6R)-2-methoxy-5-oxo-2H-pyran-6-yl]methyl 2,2-dimethylpropanoate
• CAS: 1174211-71-2
• 化学式: C₁₂H₁₈O₅
• 分子量: 242.272
• InChiKey: OAMYDNUTDNEHRO-ZJUUUORDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  methyl 6-O-trimethylacetyl-2,3-dideoxy-α-D-glycero-hex-2-enopyranosid-4-ulose 在 吡啶 、 碘 作用下， 以 四氯化碳 为溶剂， 反应 3.5h， 生成 methyl 6-O-trimethylacetyl-3-iodo-2,3-dideoxy-α-D-glycero-hex-2-enopyranosid-4-ulose
  参考文献：
  名称：

  混合路易斯酸催化的对映体纯的2和2,3-二取代的呋喃的简便合成：制备3-碘呋喃和3-（羟甲基）呋喃的简便方法

  摘要：

  对映纯呋喃合成：由混合路易斯酸（ZrCl 4 / ZnI 2）催化的对映体纯的2和2,3-二取代呋喃衍生物，包括3-碘呋喃和3-（羟甲基）呋喃衍生物描述了从商业上可获得的3,4,6- tri - O-乙酰基-D-葡萄糖的非常好的收率。该方法的主要特点是使用廉价的催化量试剂，温和的反应条件和简便的后处理程序。

  DOI：

  10.1002/chem.200900007
• 作为产物：
  描述：

  methyl 2,3-dideoxy-4,6-dihydroxy-α-D-erythro-hex-2-enopyranoside 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 methyl 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

• 2,3-Dideoxy hex-2-enopyranosid-4-uloses as promising new anti-tubercular agents: Design, synthesis, biological evaluation and SAR studies
  作者：Mohammad Saquib、Irfan Husain、Smriti Sharma、Garima Yadav、Vipul K. Singh、Sandeep K. Sharma、Priyanka Shah、Mohammad Imran Siddiqi、Brijesh Kumar、Jawahar Lal、Girish K. Jain、Brahm S. Srivastava、Ranjana Srivastava、Arun K. Shaw

  DOI：10.1016/j.ejmech.2011.03.002

  日期：2011.6

  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.
• Facile Synthesis of Enantiomerically Pure 2- and 2,3-Disubstituted Furans Catalysed by Mixed Lewis Acids: An Easy Route to 3-Iodofurans and 3-(Hydroxymethyl)furans
  作者：Mohammad Saquib、Irfan Husain、Brijesh Kumar、Arun K. Shaw

  DOI：10.1002/chem.200900007

  日期：2009.6.8

  Enantiopure furan synthesis: A synthesis, catalysed by mixed Lewis acids (ZrCl4/ZnI2), of enantiomerically pure 2‐ and 2,3‐disubstituted furan derivatives, including 3‐iodofuran and 3‐ (hydroxymethyl)furan derivatives, in good to very good yields from commercially available 3,4,6‐tri‐O‐acetyl‐D‐glucal is described. Key features of this method are the use of inexpensive reagents in catalytic amounts

  对映纯呋喃合成：由混合路易斯酸（ZrCl 4 / ZnI 2）催化的对映体纯的2和2,3-二取代呋喃衍生物，包括3-碘呋喃和3-（羟甲基）呋喃衍生物描述了从商业上可获得的3,4,6- tri - O-乙酰基-D-葡萄糖的非常好的收率。该方法的主要特点是使用廉价的催化量试剂，温和的反应条件和简便的后处理程序。