2872-68-6

Upstream product

• 106-41-2 4-bromo-phenol 
• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 
• 4163-60-4 β-D-galactose peracetate 

Downstream Products

• 903881-61-8 4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside 
• 3018-52-8 4-bromophenyl β-D-galactopyranoside 
• 903881-53-8 4-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-3'-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)biphenyl 

Relevant academic research and scientific papers

Preparation and characterization of glycopolymers with biphenyl spacers: Via Suzuki coupling reaction

Poly(vinylbiphenyl)s bearing glycoside ligands at the side chains were prepared using the Suzuku coupling reaction. Effects of glycoside reactant concentration, halide species, glycoside species, and catalyst species on the incorporation of glycoside ligand into the polymer were investigated. The obtained glycopolymers exhibited specific binding to proteins corresponding to the glycoside ligands. In addition, the biphenyl spacers formed by the Suzuki coupling reaction in the glycopolymer were fluorescent, whereas the polymer precursor was not.

O-Glycosidation reactions promoted by in situ generated silver N-heterocyclic carbenes in ionic liquids

We herein report O-glycosidation reactions promoted via silver N-heterocyclic carbene complexes formed in situ in ionic liquids. Seven different room temperature ionic liquids were screened for the glycosidation reaction of 4-nitrophenol with tetra-O-acetyl-α-d-galactopyranosyl bromide. Good to excellent yields were obtained using Ag-NHC complexes derived from imidazolium halide salts to promote the glycosidation reaction, whereas yields considered moderate to low were obtained without use of the silver carbene complex. Anion metathesis of the ionic liquids with inexpensive alkylammonium halides also resulted in silver N-heterocyclic carbene formation and subsequent O-glycosidation in the presence of silver carbonate. Effective utility of this methodology has been demonstrated with biologically relevant acceptors (including flavones and steroids) where O-β-glycoside products were obtained selectively in moderate to good yields. We have also demonstrated that the Ag-NHC complex is a superior promoter to traditionally used silver carbonate for the glycosidation of polyphenolic acceptors. The ionic liquids used in the study could be recycled three times without apparent loss in activity.

Antagonists of the myelin-associated glycoprotein: A new class of tetrasaccharide mimics

The tetrasaccharide substructure 1 of the ganglioside GQ1bα shows a remarkable affinity for the myelin-associated glycoprotein (MAG). In the search for structurally simplified and pharmacokinetically improved mimics of 1, biphenyl was identified as a feas

Synthesis of carbohydrate functionalised n-propoxy-Calix[4]arenes

The Suzuki reaction has been used to couple para-bromophenyl glycosides to boronic acid derivatives of n-propoxy-Calix[4]arene; 'a one-pot' methodology eliminates the need to isolate the boronic acids and increases the overall yield. The synthesis provides a new class of carbohydrate containing calixarenes with a deepened cavity.