2972-19-2Relevant academic research and scientific papers
Formose reactions, XXVIII. Selective formation of 2,4-bis(hydroxymethyl)-3-pentulose in N,N-dimethylformamide-water mixed solvent
Shigemasa,Ueda,Saimoto
, p. 389 - 394 (2007/10/02)
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.
Formose Reactions. Part 3. Selective Formose Reaction Catalyzed by Organic Bases
Matsumoto, Toshihiko,Inoue, Shohei
, p. 1975 - 1980 (2007/10/02)
In the formose reaction catalyzed by an organic base such as diethylaminoethanol, a compound with a potential 1,2-oxy-oxo-structure, an acceleration effect was observed on the main reaction and a suppression effect on the Cannizzaro-reaction.Organic bases with high basicity not only showed high catalytic activity but also enabled a selective formose reaction to occur, giving 2-C-(hydroxymethyl)glycerol as the main product.A mechanism to account for the formation of 2-C-(hydroxymethyl)glycerol is proposed.
