4468-72-8

Usage

Uses

Used in Organic Synthesis:
PHENYL-2,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSIDE is used as a building block in organic synthesis for the creation of various chemical compounds.
Used in Pharmaceutical Development:
PHENYL-2,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSIDE is used as a key component in the development of pharmaceuticals, contributing to the synthesis of potential drug candidates.
Used in Carbohydrate Chemistry Research:
PHENYL-2,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSIDE serves as a research tool in the study of carbohydrate chemistry, aiding scientists in understanding the structure, properties, and reactions of carbohydrates.

Upstream product

• 108-95-2 phenol 
• 604-70-6 methyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 
• 83-87-4 β-D-mannopyranose pentaacetate 
• 4163-65-9 per-O-acetyl-α-D-mannopyranose 
• 83-87-4 D-Mannose pentaacetate 
• 1095-03-0 triphenylborane 
• 3947-62-4 2,3,4,6-tetra-O-acetyl-D-mannopyranose 
• 98-80-6 phenylboronic acid 
• 19186-39-1 1,2,3,4,6-penta-O-acetyl-α-D-galactopyranose 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 604-69-3 β-D-glucose pentaacetate 
• 506-96-7 Acetyl bromide 
• 34246-15-6 phenyl glucoside 
• 108-24-7 acetic anhydride 

Downstream Products

• 3427-45-0 phenyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside 
• 76514-10-8 Acetic acid (2S,3S,4R,5R,6R)-4,5-diacetoxy-2-acetoxymethyl-2-bromo-6-phenoxy-tetrahydro-pyran-3-yl ester 
• 1464-44-4 phenyl-β-D-glucopyranoside 
• 14581-80-7 1-O-(4′-bromophenyl)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 498-07-7 levoglucosan 
• 669763-44-4 (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(4-iodophenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 22887-10-1 phenyl 4,6-O-benzylidene-β-D-glucopyranoside 
• 25876-45-3 p-hydroxyacetophenone-4-O-2',3',4',6'-tetra-O-acetyl-β-D-glucopyranoside 
• 53170-92-6 1-(4-hydroxyphenyl)-3'-oxopropyl-β-D-glucopyranose 
• 55811-42-2 methyl phenyl-β-D-glucuronate 
• 66642-78-2 4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-trans-cinnamic acid methyl ester 
• 898815-55-9 phenyl-α-D-talopyranoside 
• 1464-44-4 phenyl α-D-mannoopyranoside 

Relevant academic research and scientific papers

DETOXIFICATION OF PHENOL BY THE AQUATIC ANGIOSPERM, Lemna gibba

Lemna gibba was used to study the toxicity and metabolism of phenol. The toxicities of phenol and its major metabolite were described in terms of the effect of increasing concentrations on the vegetative reproduction of duckweed over a 7-day growth period

Phenyl glycosides – Solid-state NMR, X-ray diffraction and conformational analysis using genetic algorithm

The X-ray structures of 2,6-dimethylphenyl and phenyl 2,3,4,6-tetra-O-acetyl β-glucosides (1 and 3) and phenyl α-mannoside (6) were obtained. The independent part of the unit cell of the glycosides 1 and 6 was formed by one molecule, and for the glucoside 3, two molecules in the crystal cell were observed. In deacetylated glycosides 4 and 6 the crystal structure was established by a hydrogen bond network formed between the sugar hydroxyls and solvent molecules. The 13C CPMAS NMR spectra of aryl glycosides 1–6 were analysed. In the spectrum of 3, doubling of the C4 aryl signal was observed which confirmed the presence of two independent molecules in the solid sample. The GAAGS (Genetic Algorithm-Assisted Grid Search) method was used to determine the low-energy conformers of α-mannosides and β-glucosides. The orientation of the aryl pendant group was calculated using Molecular Mechanics (MMFF94) as well as Quantum Mechanics theory (DFT, B3LYP/6-31 + G(d,p)).

Copper-Catalyzed Anomeric O-Arylation of Carbohydrate Derivatives at Room Temperature

Direct and practical anomeric O-arylation of sugar lactols with substituted arylboronic acids has been established. Using copper catalysis at room temperature under an air atmosphere, the protocol proved to be general, and a variety of aryl O-glycosides have been prepared in good to excellent yields. Furthermore, this approach was extended successfully to unprotected carbohydrates, including α-mannose, and it was demonstrated here how the interaction between carbohydrates and boronic acids can be combined with copper catalysis to achieve selective anomeric O-arylation.

Copper-mediated anomeric: O -arylation with organoboron reagents

Copper-mediated couplings of arylboroxines with glycosyl hemiacetals furnish O-aryl glycosides via Csp2-O bond formation. The method enables the anomeric O-arylation of protected pyranose and furanose derivatives, and is tolerant of functionalized arylboroxine partners. Whereas mixtures of anomers are formed from glucopyranose, galactopyranose and arabinofuranose hemiacetals, the α-anomer is generated selectively from mannopyranose and mannofuranose-derived substrates.

Palladium-catalyzed ullmann-type reductive homocoupling of iodoaryl glycosides

A catalytic synthesis of novel biaryl-linked divalent glycosides was achieved using an electroreductive palladium-catalyzed iodoaryl-iodoaryl coupling reaction. This new method was optimized for the synthesis of divalent biaryl-linked mannopyranosides that was subsequently generalized toward several carbohydrate substrates with yields up to 96%.

Revisit of the phenol O-glycosylation with glycosyl imidates, BF 3·OEt2 is a better catalyst than TMSOTf

With BF3·OEt2 as the catalyst, the glycosylation of phenols with glycosyl trichloroacetimidates (or N-phenyl trifluoroacetimidates) bearing 2-O-participating groups leads to the desired 1,2-trans-O-glycosides in generally excellent yields without formation of the 1,2-cis-anomers. However, with TMSOTf as the catalyst, the outcomes of the corresponding phenol O-glycosylation are highly dependent on the nucleophilicity of the phenols; less nucleophilic is the phenol, higher amounts of the 1,2-cis-O-glycoside together with more side-products are generated. 1,2-Orthoesters have been found to be the major products at a low temperature (a higher temperature. BF 3·OEt2 is an effective catalyst to promote the conversion of 1,2-orthoesters into the corresponding 1,2-trans-O-glycosides. However, the 1,2-orthoesters could be converted into the dioxolenium triflate and glycosyl triflate in the presence of TMSOTf, these intermediates which might be in equilibrium with the glycosyl oxocarbenium related species lead to the final mixture of the α/β-O-glycosides and side-products.

A derivatization procedure for the simultaneous analysis of iminosugars and other low molecular weight carbohydrates by GC-MS in mulberry (Morus sp.)

Different derivatization procedures were assayed to simultaneously analyse iminosugars such as deoxynojirimycin (DNJ) or fagomine and other carbohydrates of low molecular weight by gas chromatography coupled to mass spectrometry (GC-MS) in Morus sp. Both oximation + trimethylsilylation and oximation + acetylation allowed the separation of target compounds, whereas trimethylsilyl (TMS) and acetylated derivatives showed several coelutions. Nevertheless, oximation + acetylation were discarded for giving inaccurate results for ketoses due to their incomplete derivatization. Different conditions for the conversion into trimethylsilyl oximes (TMSO) were assayed, the best results being achieved using hexamethyldisilazane with trifluoroacetic acid as silylation agent. Contents of iminosugars (DNJ, fagomine and pipecolic acid derivatives) and other carbohydrates such as mono and disaccharides, myo-inositol and galactinol isomers in mulberry extracts (fruits, leaves and branches) were determined by GC-MS using the TMSO procedure.

COMPOUNDS AND METHODS FOR TREATING BACTERIAL INFECTIONS

The present invention encompasses compounds and methods for treating urinary tract infections.

Effective friedel-crafts acylations of O- and C-arylglycosides with triflic acid

Triflic acid is well known not only as a Friedel-Crafts promoter, but also as a deglycosidation reagent. In this study, we promote effective Friedel-Crafts acylations for O- or C-arylglucosides without deglycosidation and check their inhibitory activities for β-glucosidase.

The building blocks of cellulose: The intrinsic conformational structures of cellobiose, its epimer, lactose, and their singly hydrated complexes

A combination of vibrational spectroscopy conducted under molecular beam conditions and quantum chemical calculation has established the intrinsic three-dimensional structures of the cellulose disaccharide and, focusing on the critical β1,4-linkage at the nonreducing end of the growing cellulose polymer, its C-4′ epimer. Left to their own devices they both adopt a cis (anti-φ/syn-ψ) glycosidic configuration, supported in the epimer by strong, cooperative inter-ring hydrogen bonding. In the cellulose disaccharide, however, where the OH-4′(Glc) group is equatorial, the cooperativity is reduced and the corresponding inter-ring hydrogen bonding is relatively weak. The cis conformational preference is still retained in their singly hydrated complexes. In the cellulose disaccharide insertion of the water molecule at the favored binding site between OH-4′ and the neighboring hydroxyl group OH-6′ promotes a structural reorganization to create a configuration that parallels that of its unhydrated epimer and greatly strengthens the inter-ring hydrogen bonding. In the C-4′ epimer, the axial orientation of OH-4′ blocks this binding site and the bound water molecule simply adds on at the end of the (OH-O)n chain, which has a negligible effect on the (already strong) inter-ring bonding. The implications of these results are discussed with respect to the structure and insolubility of native cellulose polymers.