4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-toluene | 94940-20-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-toluene
• 英文别名: (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(p-tolyl)tetrahydro-2H-pyran-3,4,5-triyltriacetate；(1S)-tetra-O-acetyl-1-p-tolyl-1,5-anhydro-D-glucitol；(1S)-Tetra-O-acetyl-1-p-tolyl-1,5-anhydro-D-glucit；[(2R,3R,4R,5S,6S)-3,4,5-triacetyloxy-6-(4-methylphenyl)oxan-2-yl]methyl acetate
• CAS: 94940-20-2
• 化学式: C₂₁H₂₆O₉
• 分子量: 422.432
• InChiKey: XYFBZNYJDXUVMR-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

• 作为产物：
  描述：

  β-D-葡萄糖五乙酸酯 在 乙二醇二甲醚溴化镍 、 二氢吡啶 、 [Ir(dF(CF₃)ppy)₂(dtbbpy)](PF₆) 、 四氯化钛 、 4,4'-二叔丁基-2,2'-二吡啶 、 四甲基胍 作用下， 以 氯仿 、 乙腈 为溶剂， 反应 27.0h， 生成 4-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-toluene 、 4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-toluene
  参考文献：
  名称：

  通过可见光诱导的镍催化的糖基氯化物和芳基溴化物的还原交叉偶联立体选择性制备 C-芳基糖苷

  摘要：

  已经开发了一种镍催化的糖基氯与芳基溴的交叉偶联反应。该反应在可见光照射下顺利进行，并使用了实验室稳定的糖基氯，可以高度立体选择性地合成C-芳基糖苷。

  DOI：

  10.1002/adsc.202100343

文献信息

• Process For Production Of 4-Biphenylyazetidin-2-Ones
  申请人：Lee Peter

  公开号：US20080287663A1

  公开（公告）日：2008-11-20

  The present invention relates to processes for the production of 4-biphenylylazetidin-2-one derivatives of formula

  本发明涉及生产4-联苯基氮杂环己烷-2-酮衍生物的方法。
• 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.
• The Glycosylation of Hydrocarbons by Means of the Grignard Reagent
  作者：Charles D. Hurd、William A. Bonner

  DOI：10.1021/ja01227a033

  日期：1945.11