137567-77-2

Upstream product

• 53270-12-5 1,2-O-(1-ethoxyethylene) 3,4,6-tri-O-benzyl-1-thio-α-D-glucopyranose 
• 64-19-7 acetic acid 
• 20672-66-6 3,4,6-tri-O-benzyl-D-glucopyranose 
• 75-36-5 acetyl chloride 
• 55628-54-1 3,4,6-tri-O-benzyl-D-glucal 
• 3240-34-4 [bis(acetoxy)iodo]benzene 
• 32860-96-1 3,4,6-tri-O-benzyl-1,2-O-(1-ethoxyethylidene)-β-D-mannopyranoside 
• 108-24-7 acetic anhydride 
• 16697-49-7 3,4,6-tri-O-benzyl-1,2-O-(methoxyethylidene)-β-D-mannopyranose 
• 20672-66-6 3,4,6-tri-O-benzyl-D-mannopyranose 
• 51532-75-3 3,4,6-tri-O-benzyl-1,2-O-(1-methoxyethylidene)-α-D-glucopyranose 
• 158852-31-4 3,4,6-tri-O-benzyl-1,2-O-(exo-ethoxyethylidene)-α-D-glucopyranose 
• 2754-27-0 trimethylsilyl acetate 
• 142819-21-4 ethyl 2-O-acetyl-3,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside 

Downstream Products

• 135583-76-5 Acetic acid (3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenylselanyl-tetrahydro-pyran-3-yl ester 
• 79218-68-1 2-O-acetyl-3,4,6-tri-O-benzyl-D-glucopyranose 
• 55659-53-5 1,2-di-O-acetyl-3,4,6-tri-O-benzyl-d-glucopyranose 
• 20672-66-6 3,4,6-tri-O-benzyl-D-glucopyranose 
• 912650-33-0 3,4,5,7-tetra-O-benzyl-1-deoxy-α-D-gluco-hept-2-ulosyl-(2->2)-3,4,6-tri-O-benzyl-D-glucono-1,5-lactone 
• 912650-36-3 3,4,5,7-tetra-O-benzyl-1-deoxy-α-D-galacto-hept-2-ulosyl-(2->2)-3,4,6-tri-O-benzyl-D-glucono-1,5-lactone 
• 912650-39-6 3,4,5,7-tetra-O-benzyl-1-deoxy-α-D-manno-hept-2-ulosyl-(2->2)-3,4,6-tri-O-benzyl-D-glucono-1,5-lactone 
• 205502-41-6 3,4,6-tri-O-benzyl-D-glucono-1,5-lactone 
• 108869-64-3 3,4,6-tri-O-benzyl-2-O-acetyl-α-D-glucosyl trichloroimidate 
• 460745-17-9 [(6S)-1-undecen-6-yl] 3,4,6-tri-O-benzyl-β-D-glucopyranoside 
• 460745-16-8 [(6S)-1-undecen-6-yl] 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside 
• 460745-19-1 (2R,4aR,6S,7R,8R,8aS)-6-[(2R,3R,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((S)-1-pentyl-hex-5-enyloxy)-tetrahydro-pyran-3-yloxy]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol 
• 460745-18-0 Acetic acid (2R,4aR,6S,7R,8S,8aR)-8-acetoxy-6-[(2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-((S)-1-pentyl-hex-5-enyloxy)-tetrahydro-pyran-3-yloxy]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester 
• 528603-39-6 (2R,4aR,6S,7R,8R,8aR)-6-[(2R,3R,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((S)-1-pentyl-hex-5-enyloxy)-tetrahydro-pyran-3-yloxy]-8-(4-methoxy-benzyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol 

Relevant academic research and scientific papers

Unprecedented transformation of thioglycosides to their corresponding 1-O-acetates in the presence of HClO4-SiO2

An unprecedented conversion of thioalkyl/aryl glycoside to the corresponding 1-O-acetates has been described using acetic anhydride and HClO4-SiO2 at rt. Although this transformation does not play an important role in the oligosaccha

Regio- and Stereoselective Synthesis of 1,2- cis-Glycosides by Anomeric O-Alkylation with Organoboron Catalysis

Regio- and stereoselective synthesis of 1,2-cis-glycosides has been achieved by catalytic anomeric O-alkylation using organoboron compounds. Modulating steric and electronic factors of both catalysts and substrates enables activation of the axially oriented anomeric oxygens of glucose-derived dialkoxyborates. The mild reaction conditions allow broad functional-group tolerance. This approach can be applied to the efficient sequential synthesis of oligosaccharides.

Application of the 2-nitrobenzyl group in glycosylation reactions: A valuable example of an arming participating group

The application of the o-nitrobenzyl (oNBn) group is demonstrated. This practical methodology allows the stereocontrolled synthesis of glucosides with a 1,2-trans linkage. This new ether-type arming group can broadly extend the concept of the use of participating groups in glycosylation reactions. Easy protection and deprotection of the oNBn group further confirms its usefulness in synthesis. The application of o-nitrobenzyl (oNBn) ether as an arming participating group is demonstrated. This practical methodology allows the stereocontrolled synthesis of glucosides with a 1,2-trans linkage. Copyright

Biotin sulfone tagged oligomannosides as immunogens for eliciting antibodies against specific mannan epitopes

Biotinylated tri and tetrasaccharide: α Man (1→3) α Man (1→2) α Man; α Man (1→3) α Man (1→2) α Man (1→2) α Man were prepared using methyl tertbutyl phenyl thioglycosides glycosyl donors (MBP) and biotin sulfone strategy. Three key mannosyl thioglycosidic

Armed-disarmed effect on the stability of cysteine thioglucosides

Thioglucosides of cysteine show variable stability depending on the nature of the protecting groups on the glycosyl donor. Armed protecting groups (benzyl) lead to products that decompose readily while disarmed protecting groups (acetyl) lead to more stable products. Since this armed/disarmed effect of the protecting group on the stability of the thioglucosides is more pronounced for cysteine with an unprotected carboxylic group, the proposed mechanism is that decomposition is initiated by an intramolecular protonation of glycosyl sulfide and subsequent displacement of the sulfide by adventitious nucleophiles.

Disaccharide-containing macrocycles by click chemistry and intramolecular glycosylation

In this study o- and m-xylylene moieties in combination with a triazolylmethyl moiety have been successfully employed as a relatively rigid spacer system in intramolecular glycosylation reactions. Phenyl 3,4,6-tri-O-benzyl-2-O-propargyl-1-thio-D-glucopyra

Synthetic oligosaccharides as tools to demonstrate cross-reactivity between polysaccharide antigens

Escherichia coli O148 is a nonencapsulated enterotoxigenic (ETEC) Gram negative bacterium that can cause diarrhea, hemorrhagic colitis, and hemolytic uremic syndrome in humans. The surface-exposed O-specific polysaccharide (O-SP) of the lipopolysaccharide

Synthesis of truncated analogues for studying the process of glycosyl phosphatidylinositol modification

Figure presented Many eukaryotic proteins are modified with a glycosylphosphatidylinositol (GPI) anchor at their C-termini. This post-translational modification causes these proteins to be noncovalently tethered to the plasma membrane. The synthesis of tr

Stereoselective tandem epoxidation-alcoholysis/hydrolysis of glycals with molybdenum catalysts

Molybdenum catalysts are efficient and selective catalysts for the tandem epoxidation/alcoholysis or epoxidation/hydrolysis of glucal and galactal derivatives. In glucal derivatives the selectivity is mainly controlled by the allylic substituent at position 3 of the glycal, obtaining in general the products derived from the initial formation of the α-epoxide (gluco) when this hydroxy group is protected, while products derived from the β-epoxide (manno) are mainly obtained when it is unprotected. In galactal derivatives the estereoselectivity is always high to give the α-epoxide (galacto) and independent of the protecting groups. Copyright

Concise total syntheses of aspalathin and nothofagin

Chemical Fig. Reprentation Syntheses of the C-glycosyl flavone natural products aspalathin and nothofagin have been accomplished in eight steps from tribenzyl glucal, tribenzylphloroglucinol, and either 4-(benzyloxy) phenylacetylene or 3,4-bis(benzyloxy)phenylacetylene. The key step of the syntheses involves a highly stereoselective Lewis acid promoted coupling of 1,2-di-o-acyl-3,4,6-tribenzylglucose with tribenzylphloroglucinol, which gives rise to the corresponding β-C-aryl glycoside in 30-65% yields.