thiamine propyl disulfide [methyl (dimethylphosphonodifluoromethane)phosphonate]

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: thiamine propyl disulfide [methyl (dimethylphosphonodifluoromethane)phosphonate]
• 英文别名: N-[(4-amino-2-methylpyrimidin-5-yl)methyl]-N-[(Z)-5-[[dimethoxyphosphoryl(difluoro)methyl]-methoxyphosphoryl]oxy-3-(propyldisulfanyl)pent-2-en-2-yl]formamide
• 化学式: C₁₉H₃₂F₂N₄O₇P₂S₂
• 分子量: 592.562
• InChiKey: WAMXTKUDICVQPI-VKAVYKQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  36
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  194
• 氢给体数：
  1
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  thiamine propyl disulfide [methyl (dimethylphosphonodifluoromethane)phosphonate] 在 盐酸 、 三苯基膦 作用下， 以 乙二醇二甲醚 为溶剂， 反应 0.5h， 以91%的产率得到thiamine α:β-difluoromethylenediphosphate trimethyl ester
  参考文献：
  名称：

  Synthesis of Stable Analogues of Thiamine Di- and Triphosphate as Tools for Probing a New Phosphorylation Pathway

  摘要：

  Thiamine (vitamin B1) is an essential nutritional factor metabolized inside the body in its mono-, di-, and triphosphate forms. Although the action of thiamine and thiamine diphosphate have been intensely investigated, many questions remain unanswered and the role of thiamine triphosphate is still especially unknown. To probe recent hypotheses on the implication of thiamine triphosphate in a new phosphorylation pathway involving synaptic proteins, we synthesized a series of thiamine di- and triphosphate analogues that are resistant to both enzymatic and chemical hydrolyses. The key step in the preparation of the title compounds is the coupling of thiamine propyl disulfide with adequately protected methylenebisphosphonic acid, the corresponding triphosphate analogue, and difluoromethylenebisphosphonic acid.

  DOI：

  10.1002/1521-3765(20021018)8:20<4649::aid-chem4649>3.0.co;2-m
• 作为产物：
  描述：

  thiamine propyl disulfide 、 difluoromethylenebisphosphonic acid trimethyl ester 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以66%的产率得到thiamine propyl disulfide [methyl (dimethylphosphonodifluoromethane)phosphonate]
  参考文献：
  名称：

  Synthesis of Stable Analogues of Thiamine Di- and Triphosphate as Tools for Probing a New Phosphorylation Pathway

  摘要：

  Thiamine (vitamin B1) is an essential nutritional factor metabolized inside the body in its mono-, di-, and triphosphate forms. Although the action of thiamine and thiamine diphosphate have been intensely investigated, many questions remain unanswered and the role of thiamine triphosphate is still especially unknown. To probe recent hypotheses on the implication of thiamine triphosphate in a new phosphorylation pathway involving synaptic proteins, we synthesized a series of thiamine di- and triphosphate analogues that are resistant to both enzymatic and chemical hydrolyses. The key step in the preparation of the title compounds is the coupling of thiamine propyl disulfide with adequately protected methylenebisphosphonic acid, the corresponding triphosphate analogue, and difluoromethylenebisphosphonic acid.

  DOI：

  10.1002/1521-3765(20021018)8:20<4649::aid-chem4649>3.0.co;2-m

文献信息

• Synthesis of Stable Analogues of Thiamine Di- and Triphosphate as Tools for Probing a New Phosphorylation Pathway
  作者：Emmanuel Klein、Hoàng-Oanh Nghiêm、Alain Valleix、Charles Mioskowski、Luc Lebeau

  DOI：10.1002/1521-3765(20021018)8:20<4649::aid-chem4649>3.0.co;2-m

  日期：2002.10.18

  Thiamine (vitamin B1) is an essential nutritional factor metabolized inside the body in its mono-, di-, and triphosphate forms. Although the action of thiamine and thiamine diphosphate have been intensely investigated, many questions remain unanswered and the role of thiamine triphosphate is still especially unknown. To probe recent hypotheses on the implication of thiamine triphosphate in a new phosphorylation pathway involving synaptic proteins, we synthesized a series of thiamine di- and triphosphate analogues that are resistant to both enzymatic and chemical hydrolyses. The key step in the preparation of the title compounds is the coupling of thiamine propyl disulfide with adequately protected methylenebisphosphonic acid, the corresponding triphosphate analogue, and difluoromethylenebisphosphonic acid.