161418-75-3

Upstream product

• 75-84-3 2,2-dimethyl-propanol-1 
• 532-20-7 D-arabinofuranose 
• 263243-23-8 5-azido-5-deoxy-1-O-triphenylmethyl-D-arabinitol 
• 263243-20-5 1,2,3-tri-O-acetyl-5-O-methylsulfonyl-D-arabinofuranose 
• 263243-21-6 5-azido-5-deoxy-D-arabinitol 
• 182550-30-7 5-azido-2,3,4-tri-O-benzyl-5-deoxy-D-arabinitol 
• 177567-99-6 1,2,3-tri-O-acetyl-5-azido-5-deoxy-D-arabinofuranose 
• 55287-20-2 1,2,3-tri-O-acetyl-5-hydroxy-D-arabinofuranose 
• 161512-13-6 2,3,4-tri-O-benzyl-5-benzyloxycarbonylamino-5-deoxy-D-arabinitol 
• 263243-26-1 2,3,4-tri-O-benzyl-5-benzyloxycarbonylamino-5-deoxy-β-D-arabinose 

Relevant academic research and scientific papers

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

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.

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

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.