263243-26-1Relevant articles and documents
Synthesis of ethyl 2-acetamido-6-S-(5-amino-5-deoxy-β-D- arabinopyranosyl)-2-deoxy-1,6-dithio-β-D-glucopyranoside: A sulfur-linked 5- amino-5-deoxyglycopyranosyl disaccharide
Suzuki,Hashimoto
, p. 14 - 27 (2007/10/03)
A novel pseudo-disaccharide having an imino sugar residue at the non- reducing end, namely, a sulfur-linked 5-amino-5-deoxyglycopyranosyl disaccharide, which is a potential specific inhibitor for glycosidases that recognize not only the glycosidic linkage but also the aglycone moiety, was synthesized. Glycosidation of N-Boc-5-amino-5-deoxy-D-arabinose with ethyl 2- acetamido-3,4-di-O-acetyl-2-deoxy-1,6-dithio-β-D-glucopyranoside in the presence of TsOH gave exclusively the corresponding 1,2-cis-linked thioglycoside. The interglycosidic linkage proved stable enough under conditions for the deprotection of the N-Boc group with TFA. This pseudodisaccharide was unstable at pH > 5, but stable at lower pH. The sulfur-linked 5-amino-5-deoxyglycopyranosyl disaccharide was shown to be formed from 5-amino-5-deoxy-D-arabinose and ethyl 2-acetamido-2-deoxy-1,6- dithio-β-D-glucopyranoside in an acidic buffer solution. (C) 2000 Elsevier Science Ltd.