新产品编号:698171

Chemical Name: 4-O-(2-Acetamido-4-amino-2,4,6-trideoxy-beta-D-galactopyranosyl)-2-acetamido-2-deoxy-1-O-methyl-alpha-L-altropyranosuronic acid
CAS No. 259534-62-8
项目整合开发状态: Biological Testing
项目研究机构: Hungarian Academy of Sciences (Originator), National Institutes of Health (Originator)
合成路线:The altruronic acid derivative (III) was synthesized starting from the described glycoside (I).Reduction of the azido group of (III) by hydrogenation over Pd/C provided the corresponding amine (II),which was then acylated by means of trichloroacetyl chloride and triethylamine.

合成路线:Hydrolysis of phthaloyl and acetyl groups of the galactose thioglycoside derivative (IV) by treatment with ethylenediamine afforded amine (V),which was subsequently converted to the trichloroacetamide (VI).Further acetylation of the hydroxyl group of (VI) employing Ac2O in pyridine produced the corresponding acetate ester (VII).Coupling of (VII) with the altruronic acid derivative (III) was carried out via activation of the thioglycoside by means of N-iodosuccinimide and triflic acid to furnish the fully protected disaccharide (VIII).Basic hydrolysis of the ester and amide groups of (VIII),followed by N-acetylation with Ac2O in MeOH yielded the diacetamido derivative (IX).Finally,hydrogenolytic cleavage of the O-benzyl group of (IX) with simultaneous azide reduction afforded the target disaccharide.
📌 参考资料/链接:
参考文献标题:Synthesis of the repeating unit of the O-specific polysaccharide of Shigella sonnei and quantitation of its serologic activity
文献作者:T髏h,A.; Medgyes,A.; Bajza,I.; Liptak,A.; Batta,G.; Kontrohr,T.; Peterffy,K.; Pozsgay,V.
参考来源:Bioorg Med Chem Lett 2000,10(1),19