D-glucose-6-formate | 76425-67-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: D-glucose-6-formate
• 英文别名: D-Glucopyranose, 6-formate；[(2R,3S,4S,5R)-3,4,5,6-tetrahydroxyoxan-2-yl]methyl formate
• CAS: 76425-67-7；76425-71-3；150300-80-4
• 化学式: C₇H₁₂O₇
• 分子量: 208.168
• InChiKey: CWYFXCXECHUECA-WLDMJGECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.6
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  116
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 D-glucose-6-formate 在 吡啶 作用下， 反应 4.0h， 生成 1,2,3,4-tetra-O-acetyl-6-O-formyl-D-glucopyranose
  参考文献：
  名称：

  Formylation of primary hydroxyl groups in sugars

  摘要：

  Application of 99% formic acid at 25 degrees formylates primary hydroxyl groups as shown by the easy formation of 6-O-formyl-D-glucopyranose and 6-O-formyl-D-fructofuranose, isolated as their tetra-acetates in yields of 77% and 31%, respectively. Likewise, D-glucitol gave the 2,3,4,5-tetra-O-acetyl-1,6-di-O-formyl derivative (84%) and methyl alpha-D-glucopyranoside gave the 6-formate (74%) characterized as the crystalline triacetate. On storage of the triacetate in methanol at 25 degrees, the formyl group was lost and the 2,3,6-triacetate was formed, whereas the corresponding tribenzoate was deformylated in acidic methanol without migration of the benzoyl groups.

  DOI：

  10.1016/0008-6215(90)84006-g
• 作为产物：
  描述：

  甲酸 、 D-葡萄糖 反应 3.0h， 生成 D-glucose-6-formate
  参考文献：
  名称：

  Formylation of primary hydroxyl groups in sugars

  摘要：

  Application of 99% formic acid at 25 degrees formylates primary hydroxyl groups as shown by the easy formation of 6-O-formyl-D-glucopyranose and 6-O-formyl-D-fructofuranose, isolated as their tetra-acetates in yields of 77% and 31%, respectively. Likewise, D-glucitol gave the 2,3,4,5-tetra-O-acetyl-1,6-di-O-formyl derivative (84%) and methyl alpha-D-glucopyranoside gave the 6-formate (74%) characterized as the crystalline triacetate. On storage of the triacetate in methanol at 25 degrees, the formyl group was lost and the 2,3,6-triacetate was formed, whereas the corresponding tribenzoate was deformylated in acidic methanol without migration of the benzoyl groups.

  DOI：

  10.1016/0008-6215(90)84006-g

文献信息

• Formylation of primary hydroxyl groups in sugars
  作者：Li-Xian Gan、Roy L. Whistler

  DOI：10.1016/0008-6215(90)84006-g

  日期：1990.9

  Application of 99% formic acid at 25 degrees formylates primary hydroxyl groups as shown by the easy formation of 6-O-formyl-D-glucopyranose and 6-O-formyl-D-fructofuranose, isolated as their tetra-acetates in yields of 77% and 31%, respectively. Likewise, D-glucitol gave the 2,3,4,5-tetra-O-acetyl-1,6-di-O-formyl derivative (84%) and methyl alpha-D-glucopyranoside gave the 6-formate (74%) characterized as the crystalline triacetate. On storage of the triacetate in methanol at 25 degrees, the formyl group was lost and the 2,3,6-triacetate was formed, whereas the corresponding tribenzoate was deformylated in acidic methanol without migration of the benzoyl groups.