161822-73-7

Upstream product

• 71098-88-9 N-phenylselanylphthalimide 
• 4098-06-0 triacetyl-D-galactal 
• 21193-75-9 D-galactal 
• 862851-12-5 phenyl 2-azido-2-deoxy-1-seleno-α-D-galactopyranoside 
• 100-39-0 benzyl bromide 
• 80040-79-5 3,4,6-tri-O-benzyl-D-galactal 
• 1666-13-3 diphenyl diselenide 
• 153808-91-4 Phenyl 2-azido-3,4,6-tri-O-benzyl-2-deoxy-1-seleno-α-D-galactopyranoside 
• 108-24-7 acetic anhydride 
• 190782-03-7 phenyl-2-amino-3,4,6-tri-O-benzyl-2-deoxy-1-seleno-α-D-galactopyranoside 
• 150809-76-0 phenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-1-seleno-α-D-galactopyranoside 

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 

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%).

Selenoglycosides. 3. Synthesis of Phenyl 2-(N-Acetylamino)- and 2-Azido-2-deoxy-1-seleno-α-D-glycopyranosides via Azido-phenylselenylation of Diversely Protected Glycals

Two methods are described for the preparation of diversely protected phenyl 2-azido-2-deoxy-α-D-selenoglycopyranosides from protected glycals.In the first one (method A), a peracetylated glycal is treated with sodium azide and diphenyl diselenide in the presence of (diacetoxyiodo)benzene in dichloromethane at rt.With 3,4,6-tri-O-acetyl-1,5-anhydro-2-deoxy-D-arabino-hex-1-enitol (tri-O-acetyl-D-glucal) an inseparable mixture of phenyl 2-azido-2-deoxy-α-gluco- and -α-manno-selenoglycosides is obtained (91percent yield).With 3,4,6-tri-O-acetyl-1,5-anhydro-2-deoxy-D-lyxo-hex-1-enitol (tri-O-acetyl-D-galactal) only the α-galacto isomer is obtained (92percent).Method A is not compatible with benzyl groups.In method B, a perbenzylated glycal is reacted with trimethylsilyl azide and tetra-n-butylammonium fluoride in the presence of N-phenylselenophthalimide.From protected D-glucal a gluco/manno mixture is obtained, whereas only the galacto isomer is formed from protected D-galactal (75percent yield).The compatibility of method B with a variety of protecting groups is exemplified with 6-O-acetyl, 6-O-benzyl, and 6-O-(tert-butyldimethylsilyl)-3,4-O-isopropylidene-1,5-anhydro-2-deoxy-D-lyxo-hex-1-enitol.The same diastereocontrol is observed, and the α-D-galacto isomer is obtained (60-70percent yield).Reduction of the azido group of these selenoglycosides with 1,3-propanedithiol in the presence of triethylamine and acetylation affords the corresponding phenyl 2-(N-acetylamino)-2-deoxy-α-D-selenoglycopyranosides in good yield.