200501-41-3

Basic information

• Product Name: 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl azide
• Synonyms: 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl azide
• CAS NO: 200501-41-3
• Molecular Weight: 565.669
• Mol File: 200501-41-3.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl azide(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl azide(200501-41-3)
• EPA Substance Registry System: 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl azide(200501-41-3)

Safety Data

• Hazardous Substances Data: 200501-41-3(Hazardous Substances Data)

Upstream product

• 13992-26-2 (2R,3S,4S,5R,6R)-2-(acetoxymethyl)-6-azidotetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 35899-89-9 1-amido-1-deoxygalactopyranose 
• 100-39-0 benzyl bromide 
• 3866-62-4 2,3,4,6-tetra-O-benzyl-D-galactopyranosyl acetate 
• 6386-24-9 2,3,4,6-tetra-O-benzyl-D-galactopyranose 

Relevant articles and documents

Small molecule glycoconjugates with anticancer activity

Glycoconjugates are combinations of sugar moieties with organic compounds. Due to their biological resemblance, such structures often have properties that are desirable for drugs. In this study we designed and synthesised several glycoconjugates from smal

Traceless Staudinger ligation of glycosyl azides with triaryl phosphines: Stereoselective synthesis of glycosyl amides

α-Glycosyl amides can be synthesized from the corresponding O-benzyl-α-glycosyl azides using a traceless Staudinger ligation with diphenylphosphanyl-phenyl esters 4. All the phosphines employed and their phenol precursors are stable to air at 4 °C for months. Fast intramolecular trapping of the reduction intermediates results in the direct formation of the amide link, which, in turn, prevents epimerisation and allows retention of configuration at the anomeric carbon. Yields and α-selectivity are high when the reaction is performed in polar aprotic solvents. Removal of the benzyl ether protecting groups is achieved by catalytic hydrogenation. α-Glycosyl amides represent a class of virtually unexplored nonhydrolyzable monosaccharide derivatives that may find a useful application as sugar mimics. Conformational studies by NMR spectroscopy confirm that deprotected α-glycosyl amides in the gluco, galacto, and fuco series retain the normal pyranose conformation of the monosaccharide. The reaction of phosphines 4 with tetra-O-acetyl-glycosyl azides is nonstereoconservative, and β-glycosyl amides are obtained in good yields and with complete stereoselectivity starting from both α and β azides.