190323-37-6

Upstream product

• 100351-75-5 2-(Tetraacetyl-1-β-D-glucosylsulfonyl)-pyridin 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 

Relevant academic research and scientific papers

Synthesis and characterisation of hexa- and tetrasaccharide mimics from acetobromomaltotriose and acetobromomaltose, and of C-disaccharide mimics from acetobromoglucose, obtained by electrochemical reduction on silver

Glucose-based glycomimetics characterised by a direct C-interglycosidic bond were synthesised from acetobromomaltotriose (ABMT), acetobromomaltose (ABM) and acetobromoglucose (ABG). Electroreduction on silver cathode of acetobromomaltotriose afforded the diastereoisomeric hexasaccharide mimics 1-3, which were deacetylated to 4-6. The same procedure afforded biglucosyl derivatives 10-12 from acetobromoglucose and tetrasaccharide mimics 15 and 16 from acetobromomaltose. The C-Br bond was reduced affording an intermediate anomeric radical whose coupling formed the new C-C bond. The electrochemical induced coupling resulted in a one-pot reaction to double the parent sugar units. NMR and molecular modelling were used for the conformational analysis of the diastereoisomers.

Radical dimerization of glycosyl 2-pyridylsulfones with samarium (II) iodide in the presence of HMPA

Reduction of glycosyl 2-pyridylsulfones by samarium (II) iodide in the presence of HMPA leads to glycosyl dimers in up to 74% yield. This is rationalized by a free-radical mechanism.