Nagy Veronika, Czifrák Katalin, Bényei Attila, Somsák László
Department of Organic Chemistry (POB 20), University of Debrecen, H-4010 Debrecen, Hungary.
Carbohydr Res. 2009 May 12;344(7):921-7. doi: 10.1016/j.carres.2009.02.011. Epub 2009 Feb 14.
(O-Peracylated alpha-D-gluco- and -galacto-hept-2-ulopyranosylbromide)onamides gave the corresponding (alkyl beta-D-glyco-hept-2-ulopyranoside)onamides under Koenigs-Knorr conditions, and similar aryl glycosides were obtained with sodium phenolates; (aryl and hetaryl 2-thio-beta-D-gluco-hept-2-ulopyranoside)onamides were formed with thiophenols in the presence of K(2)CO(3) in acetone, and reactions with aniline in CH(2)Cl(2) furnished (N-phenyl beta-D-glyco-hept-2-ulopyranosylamine)onamides. Some deprotected derivatives of d-gluco configuration obtained by the Zemplén protocol showed no significant inhibition against rabbit muscle glycogen phosphorylase b.
（O-过酰化α-D-葡萄糖基和半乳糖基-2-庚酮吡喃糖基溴）酰胺在柯尼希斯-克诺尔条件下生成相应的（烷基β-D-糖苷基-2-庚酮吡喃糖苷）酰胺，用酚钠可得到类似的芳基糖苷；在丙酮中，碳酸钾存在下，与硫酚反应生成（芳基和杂芳基2-硫代-β-D-葡萄糖基-2-庚酮吡喃糖苷）酰胺，在二氯甲烷中与苯胺反应得到（N-苯基β-D-糖苷基-2-庚酮吡喃糖基胺）酰胺。通过曾普伦方法得到的一些d-葡萄糖构型的脱保护衍生物对兔肌肉糖原磷酸化酶b没有显著抑制作用。
