2-octyl-4,6-di-O-acetyl-2,3-dideoxy-α-D-erythrohex-2-enopyranoside | 1119240-60-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 2-octyl-4,6-di-O-acetyl-2,3-dideoxy-α-D-erythrohex-2-enopyranoside
• 英文别名: hexyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside；[(2R,3S,6S)-3-acetyloxy-6-hexoxy-3,6-dihydro-2H-pyran-2-yl]methyl acetate
• CAS: 1119240-60-6
• 化学式: C₁₆H₂₆O₆
• 分子量: 314.379
• InChiKey: QJEFFLWFGUQRGR-XHSDSOJGSA-N

物化性质

• 沸点：
  394.0±42.0 °C(predicted)
• 密度：
  1.09±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  22
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-octyl-4,6-di-O-acetyl-2,3-dideoxy-α-D-erythrohex-2-enopyranoside 在 吡啶 、 甲醇 、 manganese(IV) oxide 、 sodium methylate 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 52.0h， 生成 [(2S,6R)-2-hexoxy-5-oxo-2H-pyran-6-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：

  乙酰化葡萄烯糖 、 正己醇 在 碘 作用下， 以 四氢呋喃 为溶剂， 生成 2-octyl-4,6-di-O-acetyl-2,3-dideoxy-α-D-erythrohex-2-enopyranoside
  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

• A convenient synthesis of pseudoglycosides via a Ferrier-type rearrangement using metal-free H3PO4 catalyst
  作者：Bala Kishan Gorityala、Shuting Cai、Rujee Lorpitthaya、Jimei Ma、Kalyan Kumar Pasunooti、Xue-Wei Liu

  DOI：10.1016/j.tetlet.2008.11.103

  日期：2009.2

  A mild and efficient synthesis of pseudoglycals has been developed using a metal-free catalytic system. Phosphoric acid proved to be an excellent catalyst for conversion of 2,4,6-tri-O-acetyl-D-glycal to 2,3-unsaturated O-glycosides. A wide range of alcohols including naturally bioactive compounds could be coupled with the glycal to give the desired products in good to excellent yields and with high levels of alpha-selectivity. (C) 2008 Elsevier Ltd. All rights reserved.
• ZnBr₂-Catalyzed and Microwave-Assisted Synthesis of 2,3-Unsaturated Glucosides of Hindered Phenols and Alcohols
  作者：D. James Bound、B. K. Bettadaiah、P. Srinivas

  DOI：10.1080/00397911.2014.909490

  日期：2014.9.2
• IBr-Catalyzed O-Glycosylation of D-Glucals: Facile Synthesis of 2,3-Unsaturated-O-glycosides
  作者：Uthaiwan Sirion、Rungnapha Saeeng、Onanong Siripru

  DOI：10.3987/com-15-13174

  日期：——

  Iodine monobromide (IBr) is explored as an alternative catalyst for the selective synthesis of 2,3-unsaturated glycosides from tri-O-acetyl-D-glucal 1 with several alcohols through Ferrier rearrangement. This reaction was shown to be a simple, efficient and cost-effective method, affords twenty examples of corresponding glycoside products in high yields with good alpha-selectivity.