88970-25-6

Upstream product

• 100-39-0 benzyl bromide 
• 5965-66-2 LACTOSE 
• 3616-19-1 lactose octaacetate 
• 108811-21-8 2,3,6-tri-O-benzyl-4-O-(2′,3′,4′,6′-tetra-O-benzyl-β-D-galactopyranosyl)-D-glucopyranose 
• 84396-49-6 allyl O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1[*]4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 108811-27-4 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl-(1→4)-2,3,6-tri-O-benzyl-β-D-glucopyranose 

Downstream Products

• 140926-89-2 2,3,6-Tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-1-C-(dichloromethyl)-α-D-glucopyranose 
• 244036-92-8 2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-D-gluconamide 
• 795306-79-5 C₆₂H₆₄O₁₀ 
• 262293-16-3 (hepta-O-benzyl-β-D-cellobiosyl)methanol 
• 140926-92-7 (1S)-(1(OH),2,4/1,3)-3,4-Di-O-benzyl-1-C-<(benzyloxy)methyl>-2-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-5-oxo-1,2,3,4-cyclohexanetetrol 
• 140926-90-5 (1R)-2,3,6-Tri-O-benzyl-1-C-(dichloromethyl)-4-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-D-glucitol 
• 140926-91-6 (1S)-(1(OH),2,4/1,3)-3,4-Di-O-benzyl-1-C-<(benzyloxy)methyl>-2-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-6,6-dichloro-5-oxo-1,2,3,4-cyclohexanetetrol 
• 193553-11-6 3-4)-tri-O-benzyl-β-D-glucopyranosyl>prop-1-ene 
• 244037-01-2 (5R,6R,7S,8R)-7,8-bis(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydro-2,3-diiodo-6-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyloxy)imidazo[1,2-a]pyridine 
• 244037-00-1 (5R,6R,7S,8S)-7,8-bis(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydro-2,3-diiodo-6-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyloxy)imidazo[1,2-a]pyridine 
• 244037-02-3 (5R,6R,7S,8S)-7,8-bis(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydro-2-iodo-6-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyloxy)imidazo[1,2-a]pyridine 
• 244037-03-4 (5R,6R,7S,8R)-7,8-bis(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydro-2-iodo-6-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyloxy)imidazo[1,2-a]pyridine 
• 245055-90-7 (Z)-5-amino-2,3,6-tri-O-benzyl-5-deoxy-4-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-D-gluconohydroximo-1,5-lactam 

Relevant academic research and scientific papers

C-Glycosyl amino acids through hydroboration-cross-coupling of exo-glycals and their application in automated solid-phase synthesis

O-Glycosylation is one of the most important post-translational modifications of proteins. The attachment of carbohydrates to the peptide backbone influences the conformation as well as the solubility of the conjugates and can even be essential for binding to specific ligands in cell-cell interactions or for active transport over membranes. This makes glycopeptides an interesting class of compounds for medical applications. To enhance the long-term availability of these molecules in vivo, the stabilization of the glycosidic bond between the amino acid residue and the carbohydrate is of interest. The described modular approach affords β-linked C-glycosyl amino acids by a sequence of Petasis olefination of glyconolactones, stereoselective hydroboration and a mild B-alkyl-Suzuki coupling reaction. The coupling products were transformed to C-glycosyl amino acid building-blocks suitable for solid-phase synthesis and successfully incorporated into a partial sequence of the tumor-associated MUC1-glycopeptide. The resulting C-glycopeptides are candidates for the development of long-term stable mimics of O-glycopeptide vaccines. Copyright

The synthesis of some epoxyalkyl β-C-glycosides as potential inhibitors of β-glucan hydrolases

The treatment of tetra-O-benzyl-D-glucono-1,5-lactone with various alkenylmagnesium halides gave the intermediate lactols which, upon reduction (Et3SiH/BF3) and protecting group manipulation, yielded alkenyl tetra-O-acetyl-β-D-C-gluc

SYNTHESIS AND CONVERSIONS OF C-(ALKYN-1-YL)-β-D-GLUCOPYRANOSIDES

A stereospecific synthesis of C-(alkyn-1-yl)-β-D-glucopyranosides from 2,3,4,6-tetrabenzyl-glucopyranolactone is reported.