161822-68-0

Upstream product

• 71098-88-9 N-phenylselanylphthalimide 
• 161822-65-7 1,5-Anhydro-2-deoxy-3,4-O-isopropylidene-6-O-(tert-butyldimethylsilyl)-D-lyxo-hex-1-enitol 
• 124477-12-9 2,6-anhydro-5-deoxy-3,4-O-isopropylidene-D-arabino-hex-5-enitol 
• 18162-48-6 tert-butyldimethylsilyl chloride 

Downstream Products

• 161822-66-8 Phenyl 6-O-acetyl-2-azido-2-deoxy-3,4-O-isopropylidene-1-seleno-α-D-galactopyranoside 
• 166828-37-1 phenyl 2-azido-2-deoxy-3,4-O-isopropylidene-1-seleno-α-D-galactopyranoside 

Relevant academic research and scientific papers

Preparation of diversely protected 2-azido-2-deoxyglycopyranoses from glycals

A new and efficient preparation of diversely protected 2-azido-2-deoxyglycopyranosides from the corresponding glycals is described. The glycals are first transformed into protected phenyl 2-azido-2-deoxy-selenoglycopyranosides by azido-phenylselenylation.

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.