Preferential formation of specific hexose and heptose in the formose reaction under microwave irradiation
Akihito Hashidzume, Toru IMAI, Nanako Deguchi, Takashi Tanibayashi, Takumi Ikeda, Tomohiro Michitaka, Satoki Kuwahara, Masaki Nakahata, Yuri Kamon, Yasuto Todokoro
Abstract
) as a catalyst at a high set temperature (150 °C) for a short time (1 min) to form preferentially specific hexose and heptose. The major products were isolated by thin layer chromatography and characterized by mass spectroscopy and NMR. These characterization data elucidated that the hexose and heptose were 2-hydroxymethyl-1,2,4,5-tetrahydroxy-3-pentanone (C6*) and 2,4-bis(hydroxymethyl)-1,2,4,5-tetrahydroxy-3-pentanone (C7*), respectively. On the basis of these observations, as well as density functional theory calculations, a plausible reaction pathway was also discussed; once 1,3-dihydroxyacetone is formed, consecutive aldol reactions favorably occur to form C6* and C7*.