(2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-(5-methylaminomethyl-furan-2-ylmethoxy)-tetrahydro-pyran-3,4,5-triol | 214146-10-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-(5-methylaminomethyl-furan-2-ylmethoxy)-tetrahydro-pyran-3,4,5-triol
• 英文别名: (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[[5-(methylaminomethyl)furan-2-yl]methoxy]oxane-3,4,5-triol
• CAS: 214146-10-8
• 化学式: C₁₃H₂₁NO₇
• 分子量: 303.312
• InChiKey: PUGPWKWKOPGBGI-LBELIVKGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  125
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-(5-methylaminomethyl-furan-2-ylmethoxy)-tetrahydro-pyran-3,4,5-triol 在 盐酸 、 溴 作用下， 以 吡啶 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.5h， 生成 5-Dimethylcarbamoyloxy-1-methyl-2-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl)-pyridinium; chloride
  参考文献：
  名称：

  Building blocks from sugars. Part 23. Hydrophilic 3-pyridinols from fructose and isomaltulose

  摘要：

  Brief exposure to bromine in water-methanol at 0 OC smoothly and effectively converts furfurylamines with hydroxymethyl (5) or glucosyloxymethyl substituents (16) into the respective 6-substituted 3-pyridinols 9 and 19, whereas the N-methyl-furfurylamines 10 and 17 elaborate the N-methyl-pyridinium betaines 13 and 22. Combination of this multistep one-pot reaction with the large scale-feasible generation of hydroxymethylfurfural (4) from D-fructose and its O-glucosyl analog 15 from isomaltulose, together with their ready conversion into furfurylamines by reductive amination, opens up a preparatively satisfactory, 3-step "reaction channel" from inexpensive sugars to hydrophilic 3-pyridinols, of interest as intermediate chemicals for drugs of the pyridostigmine type and agrochemicals. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00634-6
• 作为产物：
  描述：

  5-(α-D-glucosyloxymethyl)furfural 、 甲胺 在 镍 氢气 作用下， 以 水 为溶剂， 反应 72.0h， 以90%的产率得到(2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-(5-methylaminomethyl-furan-2-ylmethoxy)-tetrahydro-pyran-3,4,5-triol
  参考文献：
  名称：

  Building blocks from sugars. Part 23. Hydrophilic 3-pyridinols from fructose and isomaltulose

  摘要：

  Brief exposure to bromine in water-methanol at 0 OC smoothly and effectively converts furfurylamines with hydroxymethyl (5) or glucosyloxymethyl substituents (16) into the respective 6-substituted 3-pyridinols 9 and 19, whereas the N-methyl-furfurylamines 10 and 17 elaborate the N-methyl-pyridinium betaines 13 and 22. Combination of this multistep one-pot reaction with the large scale-feasible generation of hydroxymethylfurfural (4) from D-fructose and its O-glucosyl analog 15 from isomaltulose, together with their ready conversion into furfurylamines by reductive amination, opens up a preparatively satisfactory, 3-step "reaction channel" from inexpensive sugars to hydrophilic 3-pyridinols, of interest as intermediate chemicals for drugs of the pyridostigmine type and agrochemicals. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00634-6

文献信息

• Building blocks from sugars. Part 23. Hydrophilic 3-pyridinols from fructose and isomaltulose
  作者：Christoph Müller、Volker Diehl、Frieder W. Lichtenthaler

  DOI：10.1016/s0040-4020(98)00634-6

  日期：1998.9

  Brief exposure to bromine in water-methanol at 0 OC smoothly and effectively converts furfurylamines with hydroxymethyl (5) or glucosyloxymethyl substituents (16) into the respective 6-substituted 3-pyridinols 9 and 19, whereas the N-methyl-furfurylamines 10 and 17 elaborate the N-methyl-pyridinium betaines 13 and 22. Combination of this multistep one-pot reaction with the large scale-feasible generation of hydroxymethylfurfural (4) from D-fructose and its O-glucosyl analog 15 from isomaltulose, together with their ready conversion into furfurylamines by reductive amination, opens up a preparatively satisfactory, 3-step "reaction channel" from inexpensive sugars to hydrophilic 3-pyridinols, of interest as intermediate chemicals for drugs of the pyridostigmine type and agrochemicals. (C) 1998 Elsevier Science Ltd. All rights reserved.