- Synthesis of Azapyranosyl Thioglycoside: Novel Pseudo-disaccharide Having an Azasugar Residue at the Non-Reducing End
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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.
- Suzuki, Katsuhiko,Hashimoto, Hironobu
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- 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
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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.
- Suzuki,Hashimoto
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