96323-30-7

Upstream product

• 19488-48-3 methyl 2,3,6-tri-O-benzyl-α-D-galactopyranoside 
• 79218-68-1 2-O-acetyl-3,4,6-tri-O-benzyl-D-glucopyranose 
• 194807-96-0 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl fluoride 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 65827-55-6 1,2-di-O-acetyl-3,4,6-tri-O-benzyl-α-D-glucopyranoside 
• 189182-66-9 2-O-acetyl-3,4,6-tri-O-benzyl-D-glucopyranosyl trichloroacetimidate 
• 604-69-3 β-D-glucose pentaacetate 
• 100-44-7 benzyl chloride 
• 19488-49-4 methyl 2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 68779-52-2 1,2-O-(1-methoxyethylidene)-3,4,6-tri-O-benzyl-α-D-galactopyranose 
• 19488-48-3 methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside 
• 77790-46-6 1,2-di-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranose 

Downstream Products

• 117841-72-2 (2R,3R,4S,5R,6R)-3,4-Bis-benzyloxy-6-benzyloxymethyl-5-((2S,4R,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-2-methoxy-tetrahydro-pyran 

Relevant academic research and scientific papers

METHODS FOR GLYCOSYLATION

Provided herein are methods of glycosylation in the formation of disaccharides, trisaccharides, and oligosaccharides using fluoroglycosides, silyl ether glycosides and a triaryl borane catalyst.

Fluoride Migration Catalysis Enables Simple, Stereoselective, and Iterative Glycosylation

Challenges in the assembly of glycosidic bonds in oligosaccharides and glycoconjugates pose a bottleneck in enabling the remarkable promise of advances in the glycosciences. Here, we report a strategy that applies unique features of highly electrophilic b

Interrupted Pummerer Reaction in Latent-Active Glycosylation: Glycosyl Donors with a Recyclable and Regenerative Leaving Group

Latent O-glycosides, 2-(2-propylthiol)benzyl (PTB) glycosides, were converted into the corresponding active glycosyl donors, 2-(2-propylsulfinyl)benzyl (PSB) glycosides, by a simple and efficient oxidation. Treatment of the PSB donor and various acceptors with triflic anhydride provided the desired glycosides in good to excellent yields. The leaving group, which was activated by an interrupted Pummerer reaction, can be recycled (PSB-OH) and regenerated as the precursor (PTB-OH). A natural hepatoprotective glycoside, leonoside F, was efficiently synthesized in a convergent [3+1] manner with this newly developed method. The present total synthesis also led to a structural revision of this phenylethanoid glycoside.

AN EASY SYNTHESIS OF 2'-DEOXY-β-DISACCHARIDES

1,2-Di-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranose and analogs are excellent β-glycosyl donors in the presence of trimethylsilyltriflate.The resulting disaccharides are easily converted into the corresponding 2'-deoxy-β-disaccharides, opening a practical route to this important class of natural molecules.

Synthesis of O-β-D-Glucopyranosyl-(1-2)-O-β-D-glucopyranosyl-(1-6)-D-glucopyranose; Dehydrative β-D-Glucosylation Using 2-O-Acetyl-3,4,6-tri-O-benzyl-D-glucopyranose

A step-by-step synthesis of O-β-D-glucopyranosyl-(1-2)-O-β-D-glucopyranosyl-(1-6)-D-glucopyranose through the dehydrative β-D-glucosylation using 2-O-acetyl-3,4,6-tri-O-benzyl-D-glucopyranose and the ternary system of p-nitrobenzenesulfonyl chloride, silv