(2S,3R,4S,5S,6R)-6-(hydroxymethyl)-2-methoxy-2-(4-methylphenyl)oxane-3,4,5-triol | 1000878-02-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R,4S,5S,6R)-6-(hydroxymethyl)-2-methoxy-2-(4-methylphenyl)oxane-3,4,5-triol
• CAS: 1000878-02-3
• 化学式: C₁₄H₂₀O₆
• 分子量: 284.309
• InChiKey: JQWMQALMSMWOTR-RGDJUOJXSA-N

物化性质

• 沸点：
  486.8±45.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  99.4
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,3R,4S,5S,6R)-6-(hydroxymethyl)-2-methoxy-2-(4-methylphenyl)oxane-3,4,5-triol 、 对甲苯磺酰氯 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以64%的产率得到
  参考文献：
  名称：

  Remarkable β-Selectivity in the Synthesis of β-1-C-Arylglucosides:  Stereoselective Reduction of Acetyl-Protected Methyl 1-C-Arylglucosides without Acetoxy-Group Participation

  摘要：

  [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.

  DOI：

  10.1021/jo071051i
• 作为产物：
  描述：

  甲醇 、 对溴甲苯 、 2,3,4,6-四-O-三甲基硅基-D-葡萄糖酸内酯 在 正丁基锂 、 甲烷磺酸 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 21.0h， 生成 (2S,3R,4S,5S,6R)-6-(hydroxymethyl)-2-methoxy-2-(4-methylphenyl)oxane-3,4,5-triol
  参考文献：
  名称：

  Remarkable β-Selectivity in the Synthesis of β-1-C-Arylglucosides:  Stereoselective Reduction of Acetyl-Protected Methyl 1-C-Arylglucosides without Acetoxy-Group Participation

  摘要：

  [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.

  DOI：

  10.1021/jo071051i

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。