190782-03-7

Upstream product

• 153808-91-4 Phenyl 2-azido-3,4,6-tri-O-benzyl-2-deoxy-1-seleno-α-D-galactopyranoside 
• 80040-79-5 3,4,6-tri-O-benzyl-D-galactal 
• 1666-13-3 diphenyl diselenide 

Downstream Products

• 176169-12-3 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-D-galactono-1,5-lactone 
• 4171-72-6 2-acetamido-2-deoxy-3,4,6-tri-O-benzyl-D-galactopyranose 
• 161822-73-7 Phenyl 2-(N-acetylamino)-3,4,6-tri-O-benzyl-2-deoxy-1-seleno-α-D-galactopyranoside 
• 190782-06-0 C₆₁H₆₄NO₁₀PSe 
• 190782-10-6 C₆₁H₆₄NO₁₀PSe 

Relevant academic research and scientific papers

Radical mediated synthesis of N-acetyl-D-galactosamine containing C-disaccharides via a temporary phosphoramidic connection

The C-disaccharide {α-D-GalNAc-C-(1→4)-β-D-Glc-OMe} and its interglycosidic β anomer were synthesized by radical coupling of phenyl 2-amino-3,4,6-tri-O-benzyl-2-deoxy-1-seleno-α-D-galactopyranoside onto methyl 2,6-di-O-benzyl-4-deoxy-4-C-methylene- β-D-xylo-hexopyranoside, which are temporarily connected through a phosphoramido tether. A similar reaction was performed with methyl 2,3-di-O-benzyl-4-deoxy-4-C-methylene-α-D-xylo-hexopyranoside to produce the two closely related α-OMe C-disaccharides.

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%).

Stereocontrolled synthesis of 2-amino-2-deoxy-α-D-C-glycopyranosides by radical cyclization reactions

Radical cyclization of phenyl 2-N-allylamino-3,4,6-tri-O-benzyl-2-deoxy-α-D-1-seleno galacto and gluco pyranosides afforded α-D-C-glycopyranosides with high stereoselectivity involving a 5-exo-trig mechanism.