192505-47-8Relevant academic research and scientific papers
Regioselective C-3-O-acylation and O-methylation of 4,6-O-benzylidene-β-D-gluco- and galactopyranosides displaying a range of anomeric substituents
Osborn, Helen M.I.,Brome, Victoria A.,Harwood, Laurence M.,Suthers, William G.
, p. 157 - 166 (2007/10/03)
The regioselective C-3-O-acylation and O-methylation of a range of 4,6-O-benzylidene-β-D-gluco- and galactopyranosides has been studied. Regioselectivity is achieved by forming the copper chelate of the 2,3-diol using either sodium hydride and copper(II) chloride, or copper(II) acetylacetanoate, or copper(II) acetate, prior to introduction of the acylating or methylating agent.
Regioselective C-3-O-acylation and O-alkylation of 4,6-O-benzylidene-β-D-glucopyranoside derivatives displaying a range of anomeric substituents
Gridley, Jonathan J.,Osborn, Helen M.I.,Suthers, William G.
, p. 6991 - 6994 (2007/10/03)
Regioselective C-3-O-acylation and O-alkylation of ethyl 4,6-O-benzylidene-1-thio-β-D-glucopyranoside, phenyl 4,6-O-benzylidene-β-D-glucopyranoside and phenyl 4,6-O-benzylidene-1-seleno-β-D-glucopyranoside is described. Regioselectivity is obtained by first treating the benzylidene diols with sodium hydride and copper (II) chloride to form a THF soluble copper chelate.
Synthesis of a C-disaccharide glycosyl donor as a key building block for the preparation of new biologically active heparin pentasaccharide mimetics
Helmboldt, Arnim,Mallet, Jean-Maurice,Petitou, Maurice,Sinay, Pierre
, p. 1057 - 1068 (2007/10/03)
The synthesis of the C-disaccharide imidate 34, a key synthon for the synthesis of heparin pentasaccharide mimetics, is described.The C-interglycosidic bond was established through 9-endo-trig radical cyclization from two tethered monosaccharides.It was followed by conversion of the reducing end glucose unit into the required glucuronic acid derivative. - Keywords: heparin; silicon tether; radical cyclization; C-disaccharide; carbohydrate mimetics
