190323-38-7Relevant academic research and scientific papers
Radical dimerization of glycosyl 2-pyridylsulfones with samarium (II) iodide in the presence of HMPA
Doisneau, Gilles,Beau, Jean-Marie
, p. 3477 - 3480 (1998)
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.
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
Guerrini, Marco,Guglieri, Sara,Santarsiero, Roberto,Vismara, Elena
, p. 243 - 253 (2007/10/03)
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.
