219953-95-4

Upstream product

• 62867-74-7 benzyl 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 219953-91-0 benzyl-{O⁴-[O⁴,O⁶-((R)-benzylidene)-α-D-glucopyranosyl]-β-D-glucopyranoside} 
• 64656-69-5 benzyl O-α-D-glucopyranosyl-(1->4)-β-D-glucopyranoside 
• 100-51-6 benzyl alcohol 
• 57764-18-8 benzyl-[O²,O³,O⁶-triacetyl-O⁴-(tetra-O-acetyl-α-D-glucopyranosyl)-β-D-glucopyranoside] 
• 4753-07-5 α-hepta-O-acetylmaltosyl bromide 
• 100-39-0 benzyl bromide 
• 219953-93-2 benzyl 2,3,6-tri-O-benzyl-4-O-(4,6-O-benzylidene-2,3-di-O-benzyl-α-D-glucopyranosyl)-β-D-glucopyranoside 
• 132628-09-2 benzyl O-(2,3-di-O-benzyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 67398-59-8 benzyl 2,3-di-O-acetyl-4,6-O-benzylidene-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside 

Downstream Products

• 1034140-56-1 benzyl O-{2,3,6-tri-O-benzyl-4-O-[2-(3,5-diisopropyloxyphenoxy)ethyl]-α-D-glucopyranosyl}-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 1034140-57-2 benzyl O-{2,3,6-tri-O-benzyl-4-O-[2-(3,5-dibenzyloxyphenoxy)ethyl]-α-D-glucopyranosyl}-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 1034140-07-2 benzyl O-{2,3,6-tri-O-benzyl-4-O-[2-(triisopropylsilyloxy)ethyl]-α-D-glucopyranosyl}-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 1034140-55-0 benzyl O-{2,3,6-tri-O-benzyl-4-O-[2-(3,5-dimethoxyphenoxy)ethyl]-α-D-glucopyranosyl}-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 132628-10-5 benzyl O-(2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-(1->4)-O-(2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 

Relevant academic research and scientific papers

A new synthesis of the oligosaccharide domain of acarbose

Synthesis of the oligosaccharide domain of acarbose was reinvestigated and was optimally performed using a maltosidic acceptor, already bearing a α-D-Glc-(1→4)-D-Glc bond, and a new D-fucopyranosyl donor. The crucial glycosylation step was improved by varying three different parameters and notably by focusing on the C-4 protecting group of the fucosyl residue, solvent and promoter. The resulting trisaccharide was further transformed into an electrophilic species in order to open further derivatization perspectives for designing new acarbose analogues. Substitution reactions were efficiently carried out with azide and thiocyanate anions. Two other potentially interesting trisaccharidic compounds were also synthesized, i.e. the C-4 III amine and the corresponding isothiocyanate.

Dehydrative glycosylation by diethylaminosulfur trifluoride (DAST) - tin(II) trifluoromethanesulfonate-tetrabutylammonium perchlorate - triethylamine system

Dehydrative glycosylation using 2,3,4,6-tetra-O-benzyl-D-glucopyranose was carried out by the use of a condensing reagent system composed of diethylaminosulfur trifluoride (DAST), tin(II) triflate, tetrabutylammonium perchlorate, and triethylamine. Using this system, two tetrasaccharides, O- a-D-glucopyranosyl-(1→4)-O-α-D-glucopyranosyl-(1→3)-Oα-D-glucopyranosyl- (1→4)-D-glucopyranose and O-a-D-glucopyranosyl-(1→3)-O-α-D- glucopyranosyl-(1→4)-O-α-D-glucopyranosyl-(1→4)-D-glucopyranose, were synthesized.

Synthesis of the oligosaccharides alpha-D-Glcp-(1----4)-D-Xylp, alpha-D-Xylp-(1----4)-D-Glcp, alpha-D-Glcp-(1----4)-alpha-D- Glcp-(1----4)-D-Xylp, alpha-D-Glcp-(1----4)-alpha-D-Xylp-(1----4)- D-Glcp, and alpha-D-Xylp-(1----4)-alpha-D-Glcp-(1----4)-D-Glcp.

Syntheses are described of the disaccharides, alpha-D-Glcp-(1----4)-D-Xylp, alpha-D-Xylp-(1----4)-D-Glcp, and alpha-D-Xylp-(1----4)-D-Xylp, and the trisaccharides, alpha-D-Glcp-(1----4)-alpha-D-Glcp-(1----4)-D-Xylp, alpha-D-Glcp-(1----4)-alpha-D-Xylp-(1--