Synthesis of Azapyranosyl Thioglycoside: Novel Pseudo-disaccharide Having an Azasugar Residue at the Non-Reducing End

Article abstract of DOI:10.1016/S0040-4039(00)73128-5

The first synthesis of azapyranosyl pseudo-disaccharide was described.Glycosidation of N-Boc-5-amino-5-deoxy-D-arabinose with N-acetyl-6-thio-D-glucosaminide in the presence of TsOH gave the corresponding 1,2-cis linked thioglycoside exclusively.The interglycosidic linkage was proved to be stable enough for the deprotection of N-Boc group by TFA.