2-C-formyl-3,4,6 -tri-O-(p-methoxybenzyl)-D-glucal | 1125483-09-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-C-formyl-3,4,6 -tri-O-(p-methoxybenzyl)-D-glucal
• 英文别名: (2R,3S,4R)-3,4-bis((4-methoxybenzyl)oxy)-2-(((4-methoxybenzyl)oxy)methyl)-3,4-dihydro-2H-pyran-5-carbaldehyde；2-C-formyl-3,4,6-tri-O-(p-methoxybenzyl)-D-glucal
• CAS: 1125483-09-1
• 化学式: C₃₁H₃₄O₈
• 分子量: 534.606
• InChiKey: PYJWCIAOBWULAE-JFHPUIQFSA-N

物化性质

• 沸点：
  660.3±55.0 °C(predicted)
• 密度：
  1.23±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.88
• 重原子数：
  39.0
• 可旋转键数：
  14.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  81.68
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  2-C-formyl-3,4,6 -tri-O-(p-methoxybenzyl)-D-glucal 在 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 14.0h， 生成 [(1R,2S,3R)-3-[2-(dimethylamino)pyrimidin-5-yl]-2,3-bis[(4-methoxyphenyl)methoxy]-1-[(4-methoxyphenyl)methoxymethyl]propyl] methanesulfonate
  参考文献：
  名称：

  Discovery of Carbohybrid-Based 2-Aminopyrimidine Analogues As a New Class of Rapid-Acting Antimalarial Agents Using Image-Based Cytological Profiling Assay

  摘要：

  New antimalarial agents that exhibit multistage activities against drug-resistant strains of malaria parasites represent good starting points for developing next-generation antimalarial therapies. To facilitate the progression of such agents into the development phase, we developed an image-based parasitological screening method for defining drug effects on different asexual life cycle stages of Plasmodium falciparum. High-throughput screening of a newly assembled diversity-oriented synthetic library using this approach led to the identification of carbohybrid-based 2-aminopyrimidine compounds with fast-acting growth inhibitory activities against three laboratory strains of multidrug-resistant P. falciparum. Our structure-activity relationship study led to the identification of two derivatives (8aA and 11aA) as the most promising antimalarial candidates (mean EC50 of 0.130 and 0.096 mu M against all three P. falciparum strains, selectivity indices >600, microsomal stabilities >80%, and mouse malaria ED50 values of 0.32 and 0.12 mg/kg/day, respectively), targeting all major blood stages of multidrug-resistant P. falciparum parasites

  DOI：

  10.1021/jm5009693
• 作为产物：
  描述：

  4-甲氧基氯苄 在 sodium hydride 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.25h， 生成 2-C-formyl-3,4,6 -tri-O-(p-methoxybenzyl)-D-glucal
  参考文献：
  名称：

  Discovery of Carbohybrid-Based 2-Aminopyrimidine Analogues As a New Class of Rapid-Acting Antimalarial Agents Using Image-Based Cytological Profiling Assay

  摘要：

  New antimalarial agents that exhibit multistage activities against drug-resistant strains of malaria parasites represent good starting points for developing next-generation antimalarial therapies. To facilitate the progression of such agents into the development phase, we developed an image-based parasitological screening method for defining drug effects on different asexual life cycle stages of Plasmodium falciparum. High-throughput screening of a newly assembled diversity-oriented synthetic library using this approach led to the identification of carbohybrid-based 2-aminopyrimidine compounds with fast-acting growth inhibitory activities against three laboratory strains of multidrug-resistant P. falciparum. Our structure-activity relationship study led to the identification of two derivatives (8aA and 11aA) as the most promising antimalarial candidates (mean EC50 of 0.130 and 0.096 mu M against all three P. falciparum strains, selectivity indices >600, microsomal stabilities >80%, and mouse malaria ED50 values of 0.32 and 0.12 mg/kg/day, respectively), targeting all major blood stages of multidrug-resistant P. falciparum parasites

  DOI：

  10.1021/jm5009693

文献信息

• Use of XtalFluor-E as an Alternative to POCl₃ in the Vilsmeier–Haack Formylation of <i>C</i>-2-Glycals
  作者：Majdouline Roudias、Frédéric Vallée、Julien Martel、Jean-François Paquin

  DOI：10.1021/acs.joc.8b01006

  日期：2018.8.3

  We report the use of XtalFluor-E ([Et2NSF2]BF4) as an alternative to POCl3 in the Vilsmeier–Haack formylation reaction of C-2-glycals. Employing a XtalFluor-E/DMF combination allowed the desired C-2-formyl glycals to be isolated in 11–90% yield. This method was extended to the synthesis of a C-2-formylated disaccharide glycal.

  我们报告了在C -2-糖的Vilsmeier-Haack甲酰化反应中使用XtalFluor-E（[Et 2 NSF 2 ] BF 4）作为POCl 3的替代物。使用XtalFluor-E / DMF组合可以以11–90％的产率分离出所需的C -2-甲酰基乙二醇。此方法扩展到一个合成C- 2 -甲酰化二糖烯糖。
• Diastereoselective Synthesis of Polycyclic Acetal-Fused Pyrano[3,2-<i>c</i>]pyran-5(2<i>H</i>)-one Derivatives
  作者：Ram Sagar、Jongmin Park、Minseob Koh、Seung Bum Park

  DOI：10.1021/jo8023889

  日期：2009.3.6

  A facile and efficient diastereoselective one-pot synthesis of polycyclic acetal-fused pyrano[3,2-c]pyrane-5(2H)-one was achieved through the annulation reaction of 2-C-formyl glycals with various 4-hydroxycoumarins and 4-hydroxy-6-methyl-2H-pyran-2-one. The asymmetric induction was significantly influenced by the C-4 stereogenic center of 2-C-formyl glycals. The resulting polycyclic acetal-fused pyranopyrones

  一种简便和多环缩醛稠合吡喃并高效非对映选择性一锅法合成并[3,2- c ^ ]吡喃-5-（2 ħ） -酮通过2-环反应实现Ç甲酰基烯糖与各种4-羟基香豆素和4-羟基-6-甲基-2- ħ吡喃-2-酮。不对称诱导受到2- C-甲酰基糖基的C-4立体生成中心的显着影响。所得多环缩醛稠合的吡喃并吡喃酮显示出抗癌活性。