Formose reactions. XXVIII. Selective formation of 2,4-bis(hydroxymethyl)-3-pentulose in N, N-dimethylformamide-water mixed solvent.
Formose reactions. XXVIII. Selective formation of 2,4-bis(hydroxymethyl)-3-pentulose in N, N-dimethylformamide-water mixed solvent.
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形成反应。
DOI：
10.1246/bcsj.63.389
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发表时间：
1990
影响因子：
4
通讯作者：
H. Saimoto
中科院分区：
文献类型：
--
作者：
Y. Shigemasa;T. Ueda;H. Saimoto
通过选择合适的水与作为溶剂的N,N-二甲基甲酰胺的比例或合适的[硫胺素·HCl]/[HCHO]比例，在甲糖反应中有利地形成二羟基丙酮、DL-甘油四糖和2,4-双(羟甲基)-3-戊酮糖(2,4-BH-3-P)。甲醛反应受到水层中甲醛浓度的强烈影响。在所研究的反应条件下，硫胺素迅速分解。从反应混合物中分离出 2,4-BH-3-P，并通过 MS、IR 和 NMR 技术进行表征。还提出了形成 2,4-BH-3-P 的途径。
Dihydroxyacetone, DL-glycero-tetrulose, and 2,4-bis(hydroxymethyl)-3-pentulose (2,4-BH-3-P) were favorably formed in a formose reaction by choosing a suitable ratio of water to N,N-dimethylformamide used as solvent or a suitable [thiamine·HCl]/[HCHO] ratio. The formose reaction was strongly affected by the concentration of formaldehyde in the water layer. Under the reaction conditions studied, thiamine decomposed rapidly. 2,4-BH-3-P was isolated from the reaction mixture and characterized by MS, IR, and NMR techniques. A pathway for the formation of 2,4-BH-3-P was also proposed.