2,3,4,6-tetra-O-tert-butyl-D-glucono-1,5-lactone | 1006590-21-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4,6-tetra-O-tert-butyl-D-glucono-1,5-lactone
• 英文别名: (3R,4S,5R,6R)-3,4,5-tris[(2-methylpropan-2-yl)oxy]-6-[(2-methylpropan-2-yl)oxymethyl]oxan-2-one
• CAS: 1006590-21-1
• 化学式: C₂₂H₄₂O₆
• 分子量: 402.572
• InChiKey: ZNKAREIWUQGBOP-WCXIOVBPSA-N

物化性质

• 沸点：
  462.2±45.0 °C(Predicted)
• 密度：
  1.00±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  异丁烯 、 葡萄糖酸内酯 在 硫酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以60%的产率得到2,3,4,6-tetra-O-tert-butyl-D-glucono-1,5-lactone
  参考文献：
  名称：

  C-2 Epimerization of aldonolactones promoted by magnesium iodide: a new way towards non-enzymatic epimerization

  摘要：

  The first example of a non-enzymatic C-2 epimerization of aldonolactones is reported. The reaction of 2,3,4,6-tetra-O-benzyl-D-gluconolactone or 2,3,4,6-tetra-O-benzyl-D-mannonolactone with MgI2 in EtOH afforded their respective C-2 epimer. Studies conducted in EtOD showing the incorporation of a deuterium atom only at the C-2 position of the epimerized product reveal an epimerization rather than a racemization reaction. A mechanism involving a chelation with a magnesium species is proposed to explain this C-2 inversion reaction. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2007.10.006

文献信息

• C-2 Epimerization of aldonolactones promoted by magnesium iodide: a new way towards non-enzymatic epimerization
  作者：Julie Gratien、Marie-Pierre Heck、Charles Mioskowski

  DOI：10.1016/j.carres.2007.10.006

  日期：2008.1

  The first example of a non-enzymatic C-2 epimerization of aldonolactones is reported. The reaction of 2,3,4,6-tetra-O-benzyl-D-gluconolactone or 2,3,4,6-tetra-O-benzyl-D-mannonolactone with MgI2 in EtOH afforded their respective C-2 epimer. Studies conducted in EtOD showing the incorporation of a deuterium atom only at the C-2 position of the epimerized product reveal an epimerization rather than a racemization reaction. A mechanism involving a chelation with a magnesium species is proposed to explain this C-2 inversion reaction. (c) 2007 Elsevier Ltd. All rights reserved.