112289-16-4

Upstream product

• 112289-17-5 benzyl 2-O-(2-O-allyl-3,4,6-tri-O-benzyl-α-D-glucopyranosyl)-3,4,6-tri-O-benzyl-β-D-glucopyranoside 
• 100-51-6 benzyl alcohol 
• 39698-44-7 1,3,4,6-tetra-O-acetyl-2-O-allyl-α-D-glucose 
• 100662-73-5 methyl α-D-glucopyranoside 2-allyl ether 
• 112302-50-8 benzyl 3,4,6-tri-O-benzyl-2-O-(3,4,6-tri-O-acetyl-2-O-allyl-α-D-glucopyranosyl)-β-D-glucopyranoside 
• 112289-11-9 benzyl 2-O-(2-O-allyl-α-D-glucopyranosyl)-3,4,6-tri-O-benzyl-β-D-glucopyranoside 
• 112346-24-4 2-O-allyl-3,4,6-tri-O-benzyl-1-O-p-nitrobenzoyl-α-D-glucopyranose 
• 112289-19-7 2-O-allyl-3,4,6-tri-O-benzyl-α-D-glucopyranosyl bromide 
• 112346-23-3 2-O-allyl-3,4,6-tri-O-benzyl-α-D-glucopyranosyl chloride 
• 112289-13-1 (2R,3R,4S,5R,6R)-2-(acetoxymethyl)-5-(allyloxy)-6-bromo-tetrahydro-2H-pyran-3,4-diyl diacetate 
• 112289-12-0 3,4,6-tri-O-acetyl-2-O-allyl-β-D-glucopyranosyl chloride 
• 60887-19-6 2-O-allyl-3,4,6-tri-O-benzyl-α,β-D-glucopyranose 
• 55659-53-5 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-glucopyranosyl bromide 
• 58341-63-2 methyl 2-O-allyl-3,4,6-tri-O-benzyl-α-D-glucopyranoside 

Downstream Products

• 82703-59-1 benzyl O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1->2)-O-(3,4,6-tri-O-acetyl-α-D-glucopyranosyl)-(1->2)-O-(3,4,6-tri-O-benzyl-α-D-glucopyranosyl)-(1->2)-3,4,6-tri-O-benzyl-β-D-glucopyranoside 
• 112289-10-8 O-(2-O-allyl-α-D-glucopyranosyl)-(1->2)-O-(3,4,6-tri-O-benzyl-α-D-glucopyranosyl)-(1->2)-3,4,6-tri-O-benzyl-β-D-glucopyanoside 
• 112289-15-3 benzyl 2-O-(2-O-allyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-3,4,6-tri-O-benzyl-β-D-glucopyranoside 
• 112468-78-7 benzyl O-(3,4,6-tri-O-acetyl-2-O-allyl-α-D-glucopyranosyl)-(1->2)-O-(3,4,6-tri-O-benzyl-α-D-glucopyranosyl)-(1->2)-3,4,6-tri-O-benzyl-β-D-glucopyranoside 

Relevant academic research and scientific papers

Synthesis of Kojitriose using silicon-tethered glycosidation

Reaction of 3,4,6-tri-O-acetyl-β-D-glucopyranosyl chloride (1) with potassium phenylselenate gave phenyl 3,4,6-tri-O-acetyl-l-seleno-α,β-D-glucopyranoside (2) in 59% yield. Silylation of benzyl 3,4,6-tri-O-benzyl-β-D-glucopyranoside (4) with ethyl 3,4,6-tri-O-benzyl-2-O-chlorodimethylsilyl-l-thio-β-D-glucopyranoside gave benzyl 2-O-(3,4,6-tri-O-benzyl-l-S-ethyl-l-thio-β-D-glucopyranos-2-O- yldimethylsilyl)-3,4,6-tri-O-benzyl-β-D-glucopyranoside (5) in 35% yield. Reaction of 5 with W-iodosuccinimide in nitromethane gave benzyl 2-O-(3,4,6-tri-O-benzyl-α-D-glucopyranosyl)-3,4,6-tri-O-benzyl-β-D- glucopyranoside (6) in 45% yield. Chlorodimethylsilylation of phenyl 3,4,6-tri-O-acetyl-l-seleno-α-D-glucopyranoside (2α) and reaction with 6 gave benzyl 2-O-[2-O-(3,4,6-tri-O-acetyl-1-Se-phenyl-l-seleno-α-D-glucopyranos-2-O- yldimethylsilyl)-3,4,6-tri-O-benzyl-α-D-glucopyranosyl]-3,4,6-tri-O- benzyl-α-D-glucopyranoside (7) in 82% yield. Intramolecular glycosidation of 7 using N-iodosuccinimide in nitromethane gave benzyl 2-O-[2-O-(3,4,6-tri-O-acetyl-α-D-glucopyranosyl)-3,4,6-tri-O-benzyl- α-D-glucopyranosyl]-3,4,6-tri-0-benzyl-β-D-glucopyranoside (8) in 45% yield. Deprotection of 8 gave kojitriose (9) in quantitative yield. Chlorodimethylsilylation of 1,3,4,6-tetra-O-benzyl-α,β-D-fructofuranose (10) with dimethyldichlorosilane and pyridine followed by reaction with ethyl 3,4,6-tri-O-benzyl - l - thio - β - D - glucopyranoside (3) gave ethyl 2 - O - (1,3,4,6 - tetra - O - benzyl-α,β-D-fructofuranosyloxydimethylsilyl)-3,4,6-tri-O-benzyl-l- thio-β-D-glucopyranoside (11) in 85% yield. Chlorodimethylsilylation of 1,3,4,6-tetra-O-benzoyl-α-D-fructofuranose (12) with dimethyldichlorosilane and triethylamine followed by reaction with phenyl 3,4,6-tri-O-acetyl-l-thio-α-D-glucopyranoside (13) gave phenyl 2-O-(1,3,4,6-tetra-O-benzoyl-α-D-fructofuranosyloxydi-methylsilyl)-3,4,6- tri-O-acetyl-l-thio-α-D-glucopyranoside (14) in 62% yield. Both 11 and 14 failed to undergo intramolecular glycosidation. Acta Chemica Scandinavica 1996.

SYNTHESIS OF KOJITETRAOSE AND KOJIPENTAOSE

Kojitriose 2)-α-D-Glcp-(1->2)-D-Glcp>, kojitetraose, and kojipentaose have been synthesised by silver perchlorate-promoted Koenigs-Knorr type condensation, using 3,4,6-tri-O-acetyl-2-O-allyl-β-D-glucopyranosyl chloride and hepta-O-acetyl-β-k