362600-52-0

Upstream product

• 3282-30-2 pivaloyl chloride 
• 196876-47-8 phenyl 3-O-benzyl-1-thio-β-D-galactopyranoside 
• 16758-34-2 1-thiophenyl-β-D-galactopyranoside 
• 13992-16-0 1-deoxy-1-(phenylthio)-2,3,4,6-tetra-O-acetyl-β-D-galactopyranose 
• 100-39-0 benzyl bromide 

Downstream Products

• 362600-53-1 3-O-benzyl-2,4,6-tri-O-pivaloyl-α-D-galactopyranosyl fluoride 
• 362600-54-2 ethyl 6-(3-O-benzyl-2,4,6-tri-O-pivaloyl-β-D-galactopyranosyloxy)hexanoate 

Relevant academic research and scientific papers

De-O-benzylation of sterically hindered benzyl ethers

Sterically hindered benzyl ethers that cannot be removed by hydrogenolysis with a variety of catalysts are removed readily by the reaction with N-bromo-succinimide and light in the presence of aqueous calcium carbonate, a reaction developed by Binkley and Hehemann. It was found that these conditions are compatible with the presence of phthalimides and glycosyl sulfides and fluorides, in addition to the groups previously shown to be inert.

Regioselective glycosylation of glucosamine and galactosamine derivates using O-pivaloyl galactosyl donors

Penta-O-pivaloyl-galactopyranose and tetra-O-pivaloyl-galactopyranosyl bromide after electrophilic activation reacted with 6-O-protected 2-azido-galactosides to give the precursor structures of the Thomsen-Friedenreich antigen disaccharide with high regioselectivity, but low yield. With 4,6-O-benzylidene protected 2-azidogalactosides and 2-O-pivaloyl phenylthio galactosides, T-antigen disaccharides of this type were obtained in good yields. Glycosylation reactions of 4,6-O-benzylidene protected glucosamine derivatives with O-pivaloyl protected galactosyl bromide efficiently gave lactolactosamine disaccharides. Even a thioglycoside was efficiently galactosylated by this method resulting in the formation of a disaccharide thioglycoside useful itself as a potential glycosyl donor.