122220-84-2

Upstream product

• 10343-15-4 Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-allyloxy-tetrahydro-pyran-4-yl ester 
• 7464-56-4 1-O-allyl-α-D-glucopyranoside 
• 146773-64-0 allyl 2,4,6-tri-O-benzyl-β-D-glucopyranoside 
• 87908-31-4 2-methoxyethyl 2,4,6-tri-O-benzyl-β-D-glucopyranoside 
• 83921-82-8 allyl 2,4,6-tri-O-benzyl-α-D-glucopyranoside 
• 100-44-7 benzyl chloride 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 572-09-8 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide 
• 100-39-0 benzyl bromide 
• 83921-83-9 allyl O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1<*>3)-2,4,6-tri-O-benzyl-α-D-glucopyranoside 
• 114055-03-7 allyl O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1<*>3)-2,4,6-tri-O-benzyl-β-D-glucopyranoside 
• 6564-72-3 2,3,4,6-tetra-O-benzyl-D-glucopyranose 
• 146773-67-3 allyl O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1<*>3)-2,4,6-tri-O-benzyl-α-D-glucopyranoside 
• 84396-58-7 allyl O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1<*>3)-2,4,6-tri-O-benzyl-β-D-glucopyranoside 

Downstream Products

• 114055-04-8 2,4,6-tri-O-benzyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-α-D-glucopyranosyl chloride 
• 83921-68-0 benzyl O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1<*>3)-O-(2,4,6-tri-O-benzyl-β-D-glucopyranosyl)-(1<*>6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 83921-67-9 benzyl O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1<*>3)-O-(2,4,6-tri-O-benzyl-α-D-glucopyranosyl)-(1<*>6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 83921-70-4 benzyl O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1<*>3)-O-(2,4,6-tri-O-benzyl-β-D-glucopyranosyl)-(1<*>6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 83921-69-1 benzyl O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1<*>3)-O-(2,4,6-tri-O-benzyl-α-D-glucopyranosyl)-(1<*>6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 

Relevant academic research and scientific papers

Reagent Controlled Stereoselective Assembly of α-(1,3)-Glucans

Pre-activation based glycosylations have become a very powerful tool in the assembly of oligosaccharides and the use of nucleophilic additives allows for the in situ generation of reactive intermediates with tailored reactivity. We here use a glycosylation strategy that is based on the use of per-benzylated imidate building blocks for the fully stereoselective construction of a spacer equipped Aspergillus fumigatus α-1,3-octaglucan. We have used the trimethylsilyl iodide (TMSI)-triphenylphosphine oxide (Ph3P=O) for the stereoselective installation of an azidopropanol spacer and triflic acid (TfOH)-dimethyl formamide (DMF) enabled glycosylations for the coupling reactions with the secondary glucosyl C-3-alcohols. An operationally simple in situ activation coupling procedure is introduced and used for the final glycosylation events towards the octasaccharide.

Dehydrative Glycosylation Using Heptabenzyl Derivatives of Glucobioses and Lactose

Dehydrative glycosylations of the 2-, 3-, 4-, and 6-OH groups of D-glucopyranose with hepta-O-benzyl derivatives of glucobioses (O-D-glucopyranosyl-(1->n)-D-glucopyranose; n = 2, 3, 4, or 6) and lactose, in the presence of a ternary mixture of p-nitrobenzenesulfonyl chloride, silver trifluoromethanesulfonate, and triethylamine in dichloromethane showed that the selectivity of the reaction depended on the anomeric configuration and the linking position to the reducing tribenzylglucose moiety of the nonreducing tetrabenzylglucosyl residue and on the class of the OH group to be glycosylated.The use of a quaternary mixture of p-nitrobenzenesulfonyl chloride, silver trifluoromethanesulfonate, N,N-dimethylacetamide, and triethylamine made all but the β(1->2)-linked biosyl donor undergo α-condensation.Several new linear trisaccharides were obtained via debenzylation of the condensates.

STEREOSELECTIVITY IN THE DEHYDRATIVE GLYCOSYLATION WITH HEPTA-O-BENZYL-GLUCOBIOSES

Dehydrative glycosylation of benzyl 2,3,4-tri-O-benzyl α-D-glucopyranoside with hepta-O-benzyl-kojibiose, -sophorose, -nigerose, -laminaribiose, -maltose, -cellobiose, -isomaltose, and -gentiobiose gave 16 linear trisaccharide derivatives.The reaction of α(1->2)-, β(1->3)-, α(1->4)-, and β(1->6)-linked biose derivatives shows the α-selectivity, while the reaction of the others does the β-selectivity.