3256-10-8

Upstream product

• 82186-24-1 benzyl 2,4-di-O-benzyl-3,6-di-O-β-D-glucopyranosyl-α-D-glucopyranoside 
• 186697-04-1 benzyl 4,6-O-benzylidene-α-D-glucopyranoside 
• 34246-23-6 benzyl D-glucopyranoside 
• 50-99-7 D-glucose 
• 77988-18-2 benzyl O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1-3)-O-<2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl-(1-6)>-2,4-di-O-benzyl α-D-glucopyranoside 
• 82186-23-0 benzyl 2,4-di-O-benzyl-3,6-di-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-α-D-glucopyranoside 
• 75547-73-8 6²-β-D-glucopyranosyl-laminaratriose 
• 82228-12-4 benzyl 2,4-di-O-benzyl-α-D-glucopyranoside 
• 82228-11-3 benzyl 2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside 

Relevant academic research and scientific papers

Stereoselective α-Glucosylation with Tetra-O-benzyl-α-D-glucose and a Mixture of Trimethylsilyl Bromide, Cobalt(II) Bromide, Tetrabutylammonium Bromide, and a Molecular Sieve. A Synthesis of 3,6-Di-O-(α-D-glucopyranosyl)-D-glucose

A mixture of trimethylsilyl bromide, cobalt(II) bromide, tetrabutylammonium bromide, and a molecular sieve (4A) is effective for the stereoselective, one-stage α-glucosylation of alcohol with 2,3,4,6-tetra-O-benzyl-α-D-glucopyranose in dichloromethane.Using this procedure, several disaccharide derivatives as well as O-α-D-glucopyranosyl-(1 -> 3)-O- 6)>-D-glucopyranose are synthesized.

SYNTHESIS OF A BRANCHED D-GLUCOTETRAOSE, THE REPEATING UNIT OF THE EXTRACELLULAR POLYSACCHARIDES OF Grifola umbellate, Sclerotinia libertiana, Porodisculus pendulus, AND Schizophyllum commune FRIES

The synthesis of D-glucotetraose, 3-O--6-O-β-D-glucopyranosyl-α (and β)-D-glucopyranose, the repeating unit of the extracellular polysaccharides of Grifora umbellata, Sclerotinia libertiana, Porodisculus pendulus, and Schizophyllum commune Fries, is described.

ONE-STAGE GLYCOSYLATION USING PROTECTED GLYCOSE: THE SYNTHESIS OF O-β-D-GLUCOPYRANOSYL-(1->3)-O-6)>-D-GLUCOPYRANOSE

The one-stage β-glycosilation of benzyl 3-O-acetyl-2,4-di-O-benzyl-α-D-glucopyranoside ( 1 ) with 2,3,4,6-tetra-O-benzyl-α-D-glucopyranose ( 2 ) using a mixture of p-nitrobenzenesulfonyl chloride, silver trifluoromethanesulfonate, and triethylamine, followed by deacetylation, gave benzyl O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1->6)-2,4-di-O-benzyl-α-D-glucopyranoside ( 3 ).The disaccharide derivative 3 was then subjected to the β-glucosylation, followed by catalytic hydrogenation, to afford O-β-D-glucopyranosyl-(1->3)-O-6)>-D-glucopyranose ( 4 ).The key intermediate 1 was prepared from D-glucose by way of a Fischer reaction, triphenylmethylation, a controlled benzylation, and detriphenylmethylation.