161822-70-4

Upstream product

• 108-24-7 acetic anhydride 
• 150809-70-4 Phenyl 2-azido-2-deoxy-3,4,6-tri-O-benzyl-1-seleno-α-D-glucopyranoside 

Downstream Products

• 4171-79-3 N-((3R,4R,5S,6R)-4,5-bis(benzyloxy)-6-(benzyloxymethyl)-2-hydroxy-tetrahydro-2H-pyran-3-yl)acetamide 
• 34051-37-1 2-Acetamido-3,4,6-tri-O-benzyl-2-deoxy-D-glucono-1,5-lacton 

Relevant academic research and scientific papers

Convenient preparation of perbenzylated 2-Azido and 2-N-acetylamino-2-deoxy-D-hexono-1,5-lactones by oxidation of the corresponding lactols

2-Azido-3,4,6-tri-O-benzyl-2-deoxy-D-galacto, gluco and mannopyranoses (1, 2, 3) were oxidized with DMSO in the presence of acetic anhydride. From 1 and 2 the corresponding lactone derivatives were obtained in good yield (89-92%), whereas from 3, glucono-1,5-lactone was obtained (92%) after complete epimerization at C-2. 2-N-Acetylamino-3,4,6-tri-O-benzyl-2-deoxy-D-galacto, gluco and mannopyranoses (7, 8, 9) were obtained from the corresponding 2-azido phenylselenoglycopyranosides (13, 14, 15) by reduction, N-acetylation and hydrolysis catalyzed by mercury trifluoroacetate. Oxidation of 7 and 8 by tetra-n-propylammonium tetra-oxoruthenate (VII) in the presence of 4-methylmorpholine-N-oxide afforded the corresponding lactones in good yield (90%) and high purity. Epimerization at C-2 occurred during oxidation of 9 and perbenzylated D-glucono-1,5-lactone (11) was obtained (90%).