130050-83-8

Upstream product

• 34234-44-1 methyl 2,3,4-tri-O-benzoylglucopyranoside 
• 1521271-14-6 3,3-difluoro-3H-indol-2-yl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 920749-29-7 Pent-4-enoic acid (3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester 
• 90357-89-4 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl trichloroacetimidate 
• 74808-09-6 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl trichloroacetimidate 
• 78153-79-4 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl fluoride 
• 74666-83-4 1-deoxy-1-(S-ethyl)-2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside 
• 34234-44-1 methyl 2,3,4-tri-O-benzoyl-α-D-mannopyranoside 
• 779352-70-4 2,3,4,6-tetra-O-benzyl-α-mannopyranosyl benzyl phthalate 
• 74666-83-4 S-ethyl 2,3,4,6-tetra-O-benzyl-1-deoxy-1-thio-α-D-mannopyranoside 
• 4196-35-4 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl bromide 
• 100-39-0 benzyl bromide 
• 13265-84-4 D-glucal 

Relevant academic research and scientific papers

Catalytic and stereoselective glycosylation with glycosyl N-trichloroacetylcarbamate

Catalytic and stereoselective glycosylation efficiently proceeded by activating a glycosyl N-trichloroacetylcarbamate with a catalytic amount of Lewis acids in the presence of a glycosyl acceptor and molecular sieves 5 ?. Catalytic and one-pot dehydrative

Trityl tetrakis(pentafluorophenyl)borate catalyzed stereoselective glycosylation using glycopyranosyl fluoride as a glycosyl donor

A catalytic and stereoselective glycosylation of glycosyl fluorides with several glucosides is successfully performed by using a catalytic amount of trityl tetrakis(pentafluorophenyl) borate.

A Mechanistic Probe into 1,2-cis Glycoside Formation Catalyzed by Phenanthroline and Further Expansion of Scope

Phenanthroline, a rigid and planar compound with two fused pyridine rings, has been used as a powerful ligand for metals and a binding agent for DNA/RNA. We discovered that phenanthroline could be used as a nucleophilic catalyst to efficiently access high

A visible light promoted O-glycosylation with glycosyl trichloroacetimidates using eosin Y as an organo photoacid

A photoacid catalyzed O-glycosylation of alcohols with glycosyl trichloroacetimidates in the presence of commercially available phenolic photoacids, fluorescein, 4′,5′-dibromo-fluorescein, and eosin Y under visible light irradiation by blue LEDs was devel

Visible light promoted method for constructing O-glycoside bonds

The invention discloses a visible light promoted method for constructing O-glycoside bonds. Glycosyl trichloroacetimidate is taken as a donor, and phenolic compounds are taken as a photocatalyst; a molecular sieve is added; and the O-glycoside bonds are g

Glycosylation with 3,5-Dimethyl-4-(2′-phenylethynylphenyl)phenyl (EPP) Glycosides via a Dearomative Activation Mechanism

A highly effective and versatile glycosylation method is developed, which uses 3,5-dimethyl-4-(2′-phenylethynylphenyl)phenyl (EPP) glycosides as donors and NIS/TMSOTf as promoter and proceeds via an unprecedented dearomative activation mechanism.

N-Trifluoromethylthiosaccharin/TMSOTf: A New Mild Promoter System for Thioglycoside Activation

For the first time, N-trifluoromethylthiosaccharin was used to activate thioglycosides in the presence of catalytic amounts of TMSOTf. The results show that the activated thioglycosides undergo glycosidation reactions with various glycosyl acceptors to gi

α-Selective Glycosylation with β-Glycosyl Sulfonium Ions Prepared via Intramolecular Alkylation

Stereoselective glycosylation remains the main challenge in the chemical synthesis of oligosaccharides. Herein we report a simple method to convert thioglycosides into β-sulfonium ions via an intramolecular alkylation reaction, leading to highly α-selective glycosylations for a variety of glycosyl acceptors. The influence of the thioglycoside substituent and the protecting group pattern on the glycosyl donor was investigated and showed a clear correlation with the observed stereoselectivity.

Nucleofuge Generating Glycosidations by the Remote Activation of Hydroxybenzotriazolyl Glycosides

Hydroxybenzotriazole is routinely used in peptide chemistry for reducing racemization due to the increased reactivity. In this article, very stable hydroxybenzotriazolyl glucosides were identified to undergo glycosidation. The reaction was hypothesized to go through the remote activation by the Tf2O at the N3-site of HOBt followed by the extrusion of the oxocarbenium ion that was attacked by the glycosyl acceptor. Further, equilibration of the zwitterionic benzotriazolyl species makes the leaving group noncompetitive and generates the nucleofuge that has been reconverted to the glycosyl donor. The reaction is mild, high yielding, fast and suitable for donors containing both C2-ethers and C2-esters as well. The regenerative-donor glycosidation strategy is promising as it enables us to regenerate the glycosyl donor for further utilization. The utility of the methodology for the oligosaccharide synthesis was demonstrated by the successful synthesis of the branched pentamannan core of the HIV1-gp120 complex.

AuCl3-AgOTf promoted O-glycosylation using anomeric sulfoxides as glycosyl donors at room temperature

Activation of sulfoxide as glycosyl donors using AuCl3/AgOTf reagent system has been described. Under optimal reaction conditions, both armed and disarmed glycosyl sulfoxide donors were found to react with a range of primary, secondary, and tertiary alcohol acceptors, and sugar derived glycosyl acceptors to afford the corresponding glycosides in moderate to good yields with predictable selectivity. The reactions are quick (20–60 min), facile at room temperature and the reactions conditions tolerate acid sensitive groups.