98906-48-0

Upstream product

• 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 
• 55659-53-5 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-glucopyranosyl bromide 
• 108869-64-3 3,4,6-tri-O-benzyl-2-O-acetyl-α-D-glucosyl trichloroimidate 
• 3254-17-9 3,4,6-tri-O-acetyl-1,2-O-(1-ethoxyethylidene)-α-D-glucopyranose 
• 79218-68-1 2-O-acetyl-3,4,6-tri-O-benzyl-D-glucopyranose 
• 19488-48-3 methyl 2,3,6-tri-O-benzyl-α-D-galactopyranoside 
• 38184-00-8 3,4,6-Tri-O-acetyl-1,2-O-<1-(exo-isopropoxy)ethylidene>-α-D-glucopyranose 
• 100-39-0 benzyl bromide 
• 666706-54-3 3,4,6-tri-O-benzyl-1,2-O-(exo-trifluoroethoxyethylidene)-α-D-glucopyranose 
• 666706-55-4 3,4,6-tri-O-benzyl-1,2-O-(exo-isopropyloxyethylidene)-α-D-glucopyranose 
• 158852-31-4 3,4,6-tri-O-benzyl-1,2-O-(exo-ethoxyethylidene)-α-D-glucopyranose 
• 68779-52-2 1,2-O-(1-methoxyethylidene)-3,4,6-tri-O-benzyl-α-D-galactopyranose 
• 604-69-3 β-D-glucose pentaacetate 

Downstream Products

• 213028-99-0 Trifluoro-methanesulfonic acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-((2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl ester 
• 98906-49-1 methyl 3,4,6-tri-O-benzyl-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside 
• 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

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

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.

One-Pot Relay Glycosylation

A novel one-pot relay glycosylation has been established. The protocol is characterized by the construction of two glycosidic bonds with only one equivalent of triflic anhydride. This method capitalizes on the in situ generated cyclic-thiosulfonium ion as the relay activator, which directly activates the newly formed thioglycoside in one pot. A wide range of substrates are well-accommodated to furnish both linear and branched oligosaccharides. The synthetic utility and advantage of this method have been demonstrated by rapid access to naturally occurring phenylethanoid glycoside kankanoside F and resin glycoside merremoside D.

Dehydrative Glycosylation Enabled by a Comproportionation Reaction of 2-Aryl-1,3-dithiane 1-Oxide?

A new dehydrative glycosylation reaction has been established by capitalizing on the comproportionation reaction of 2-aryl-1,3-dithiane 1-oxides promoted by triflic anhydride (Tf2O). By wedding the high potency of thiophilic promoter system with the step efficiency of dehydrative glycosylation, this reagent underwent facile intermolecular oxothio acetalization with C1-hemiacetal donor to install a temporary leaving group, rendering a transient electrophilic center at the remote site to the anomeric position. The sulfenyl triflate tethered at the terminus concomitantly activated the sulfide intramolecularly to afford the oxocarbenium ion, thereby facilitating the title glycosylation. Aside from accommodating broad range functional groups and inactive hemiacetal substrates, the present activation protocol also proved expedient for 1,3-diol protection. Most importantly, this method further provided a fresh perspective for the application of sulfur chemistry to carbohydrate chemistry.

MPTGs: Thioglycoside Donors for Acid-Catalyzed O-Glycosylation and Latent-Active Synthetic Strategies

4-(p-Methoxyphenyl)-4-pentenylthioglycosides (MPTGs) undergo acid-catalyzed O-glycosylation with a range of alcohol acceptors in the presence of 10 mol % of triflic acid at room temperature. Particularly encouraging is the reactivity of MPTGs toward unrea

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.

Comparative solution and solid-phase glycosylations toward a disaccharide library

A comparative study on solution-phase and solid-phase oligosaccharide synthesis was performed. A 16-member library containing all regioisomers of Glc-Glc, Glc-Gal, Gal-Glc, and Gal-Gal disaccharides was synthesized both in solution and on solid phase. The

Glycosyl trichloroacetylcarbamate: A new glycosyl donor for O-glycosylation

Glycosyl trichloroacetylcarbamates, readily obtained by reacting 1-hydroxy sugars with trichloroacetylisocyanate, have been found as excellent glycosyl donors, and the corresponding O-glycosides are formed in good to excellent yields with a fairly good degree of selectivity.

Stereospecific access to β-mannosides from glucose-derived 1,2-orthoesters as glycosyl donors

A new, stereospecific synthesis of β-mannosides from glucose-derived 1,2-orthoesters has been developed by a simple four step procedure, comprising β-specific glycosidation of the 1,2-orthoesters, 2′-O-deacetylation, 2′-O-triflation, and SN 2 type inversi

A practical synthesis of β-D-mannopyranosides

An indirect yet highly efficient protocol for the β-D-mannosylation of sterically hindered alcohols is reported. Trichloroacetimidate 5 is used a key building block which is converted into the desired mannosides 9 via triflates 8 by an ultrasound promoted