321679-30-5

Upstream product

• 100-52-7 benzaldehyde 
• 54400-75-8 allyl 2-acetamido-2-deoxy-β-D-glucopyranoside 
• 63064-48-2 allyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside 
• 3068-34-6 Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester 
• 63064-49-3 allyl 2-acetamido-(R)-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 
• 321679-22-5 (R)-2,3-epoxypropyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 

Relevant academic research and scientific papers

Stereoselective synthesis of epoxyalkyl glycoside precursors of glycosyl glycerol analogues from alkenyl glycosides of N-acetyl-D-glucosamine derivatives

The synthesis of epoxyalkyl glycoside derivatives of N-acetyl-D-glucosamine is described. Epoxidation of the corresponding alkenyl glycosides with m-CPBA took place with different stereoselectivity depending on the nature of the unsaturated system and the protecting groups on the sugar moiety. The configuration of the newly formed stereogenic centres has been confirmed unequivocally by chemical correlation.

Potential anticancer drugs, 4 - Glycosyl glycerol derivatives as drug carrier system. Stereoselective synthesis of epoxyalkyl N-acyl-β-D-glucopyranosides and their reactivity with nucleophiles

The synthesis of alkenyl 2-acylamino-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosides from N-acetyl-D-glucosamine is described. The oxidation of alkenyl glycosides with m-CPBA gives the corresponding oxiranes in good yields, and with high stereoselectivity. Analogues of glycosyl glycerol derivatives, which can be used as drug carriers, were obtained by various ring-opening reactions with different nitrogen, sulfur, and carbon nucleophiles.