2-(2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl)toluene | 94940-18-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl)toluene
• 英文别名: 2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-toluene；(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2-toluene；(1S)-tetra-O-acetyl-1-o-tolyl-1,5-anhydro-D-glucitol；(1S)-Tetra-O-acetyl-1-o-tolyl-1,5-anhydro-D-glucit；[(2R,3R,4R,5S,6S)-3,4,5-triacetyloxy-6-(2-methylphenyl)oxan-2-yl]methyl acetate
• CAS: 94940-18-8
• 化学式: C₂₁H₂₆O₉
• 分子量: 422.432
• InChiKey: KZQDUGUQEAPTFD-TXVWBRJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-(2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl)toluene 在 四氯化碳 、 溴 、 碘 作用下， 生成 (1S)-tetra-O-acetyl-1-(5-bromo-2-methyl-phenyl)-1,5-anhydro-D-glucitol
  参考文献：
  名称：

  Shdanow; Dorofeenko, Doklady Akademii Nauk SSSR, 1957, vol. 112, p. 433

  摘要：

  DOI：
• 作为产物：
  描述：

  2,3,4,6-四乙酰氧基-alpha-D-吡喃葡萄糖溴化物 在 吡啶 、 magnesium 作用下， 反应 5.0h， 生成 2-(2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl)toluene
  参考文献：
  名称：

  Panigot, Michael J.; Curley, Robert W., Journal of Carbohydrate Chemistry, 1994, vol. 13, # 2, p. 293 - 302

  摘要：

  DOI：

文献信息

• Synthesis of Aryl <i>C</i>-Glycosides via Iron-Catalyzed Cross Coupling of Halosugars: Stereoselective Anomeric Arylation of Glycosyl Radicals
  作者：Laksmikanta Adak、Shintaro Kawamura、Gabriel Toma、Toshio Takenaka、Katsuhiro Isozaki、Hikaru Takaya、Akihiro Orita、Ho C. Li、Tony K. M. Shing、Masaharu Nakamura

  DOI：10.1021/jacs.7b03867

  日期：2017.8.9

  We have developed a novel diastereoselective iron-catalyzed cross-coupling reaction of various glycosyl halides with aryl metal reagents for the efficient synthesis of aryl C-glycosides, which are of significant pharmaceutical interest due to their biological activities and resistance toward metabolic degradation. A variety of aryl, heteroaryl, and vinyl metal reagents can be cross-coupled with glycosyl

  我们开发了一种新型的非对映选择性铁催化的各种糖基卤化物与芳基金属试剂的交叉偶联反应，用于有效合成芳基 C-糖苷，由于它们的生物活性和对代谢降解的抵抗力，它们具有重要的药学价值。在由氯化铁 (II) 和庞大的双膦配体 TMS-SciOPP 组成的明确定义的铁络合物的存在下，各种芳基、杂芳基和乙烯基金属试剂可以与糖基卤化物以高产率交叉偶联。该反应的化学选择性允许使用合成通用的乙酰保护糖基供体，并在芳基部分结合各种官能团，产生多种芳基 C-糖苷，包括 Canagliflozin、一种钠-葡萄糖协同转运蛋白 2 (SGLT2) 抑制剂和一种流行的糖尿病药物。交叉偶联反应通过糖基自由基中间体的生成和立体选择性捕获进行，代表了基于铁催化的高度立体选择性碳-碳键形成的罕见例子。使用 3,4,6-tri-O-acetyl-2-O-allyl-α-d-glupyranosyl bromide (8) 和 6-bromo-1-hexene
• Remarkable β-Selectivity in the Synthesis of β-1-<i>C</i>-Arylglucosides:  Stereoselective Reduction of Acetyl-Protected Methyl 1-<i>C</i>-Arylglucosides without Acetoxy-Group Participation
  作者：Prashant P. Deshpande、Bruce A. Ellsworth、Frederic G. Buono、Annie Pullockaran、Janak Singh、Thomas P. Kissick、Ming-H. Huang、Hildegard Lobinger、Theodor Denzel、Richard H. Mueller

  DOI：10.1021/jo071051i

  日期：2007.12.1

  [GRAPHICS]An efficient and practical process to generate beta-C-arylglucoside derivatives was achieved. The process described involves Lewis acid mediated ionic reduction of a peracetylated 1-C-aryl methyl glucoside derived from the addition of an aryl-Li to selectively protected delta-D-gluconolactone. The reduction of the 2-acetoxy-1-C-oxacarbenium ion intermediates proceeds with a high degree of selectivity to give beta-C-arylglucosides without 2-acetoxy group participation. Furthermore, during the reduction process we also identified an unprecedented critical role of water. By changing from the usual benzyl ether protecting groups because of cost and chemical compatibility concerns, the new process is made additionally efficient and highly selective.