Arylsulfuryl Chlorideによるアルコール類の硫酸エステル化(第1報) : 単糖のMonosulfation

抄録

The authors found that arylsulfuryl chlorides can be used as mild sulfating agents, and they are applied to the monosulfation of monosaccharides. Among the six kinds of arylsulfuryl chlorides used 2, 4, 6-trichlorophenylsulfuryl chloride showed a low reactivity, while the rest of five showed the similar degree of reactivity. Phenylsulfuryl chlorides (PSC) was found to be the most practical agent from economical and productive point of view. Monosulfation of five hexoses and four pentoses with PSC under a suitable reaction condition (monosaccharide : PSC : pyridine=1 : 1 : 1 in molar ratio at 25° for 8hr.) gave only monosulfates of the primary hydroxyls. This fact was confirmed by the studies of methylation as well as periodate oxidation.