3427-45-0

Usage

Uses

Used in Organic Chemistry Research:
PHENYL 2,3,4,5-TETRA-O-ACETYL-ALPHA-D-GLUCOPYRANOSIDE is used as a building block for the synthesis of various glycosides and carbohydrate derivatives, contributing to the development of new compounds with potential applications in various fields.
Used in Pharmaceutical and Biochemical Applications:
PHENYL 2,3,4,5-TETRA-O-ACETYL-ALPHA-D-GLUCOPYRANOSIDE is used as a potential pharmacological and therapeutic agent due to its ability to interact with biological systems. Further research is required to fully understand its properties and explore its potential uses in medicine and biochemistry for the development of new drugs and therapies.

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 
• 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 
• 3867-86-5 Brigl's anhydride 
• 604-70-6 Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-methoxy-tetrahydro-pyran-4-yl ester 
• 604-69-3 β-D-glucose pentaacetate 
• 604-68-2 α-D-glucopyranose peracetylate 
• 5435-44-9 (E)-3-Ureido-but-2-enoic acid ethyl ester 
• 4468-72-8 phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 

Downstream Products

• 1464-44-4 phenyl α-D-mannoopyranoside 
• 898815-55-9 phenyl-α-D-talopyranoside 
• 3149-61-9 Phenyl-(tetra-O-methyl-α-D-glucopyranosid) 
• 34168-82-6 1-O-(4′-bromophenyl)-2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside 
• 4630-62-0 phenyl-α-D-glucopyranoside 
• 669763-42-2 (4-iodo-phenyl)-(tetra-O-acetyl-α-D-glucopyranoside) 
• 111137-95-2 phenyl 4,6-O-benzylidene-1-O-α-D-glucopyranoside 
• 219536-52-4 phenyl 2-O-acetyl-4,6-O-benzylidene-1-O-α-D-glucopyranoside 

Relevant academic research and scientific papers

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.

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-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.

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.

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%.

COMPOUNDS AND METHODS FOR TREATING BACTERIAL INFECTIONS

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

Stereoselectivity of reactions at the glycoside center of carbohydrates: VII. Synthesis of aryl α- and -β-D-glucopyranosides by Helferich, catalyzed by boron trifluoride etherate

13C NMR spectroscopy was used to study the stereoselectivity of glycosylation of phenols with the α and β anomers of penta-O-acetyl-D-glucopyranose, penta-O-trifluoroacetyl-D-glucopyranose, and 2,3,4,6-tetra-O-acetyl-1-O-trifluoroacetyl-D-glucopyranose in the presence of boron trifluoride etherate at varied temperature, time, and catalyst amount. The boron trifluoride etherate-catalyzed reaction of penta-O-acetyl-β -D-glucopyranose and 2,3,4,6-tetra-O-acetyl-1-O-trifluoroacetyl-β -D-glucopyranose with phenols occurs with a high stereocontrol to give, depending on conditions, predominantly 1,2-cis- or 1,2-trans-aryl-glycosides. This reaction can be used for preparative synthesis of the α- and β-anomeric forms of glycosides of a wide range of phenols.

The catalytic synthesis of aryl O-glycosides using triaryloxyboranes

Triaryloxyboranes worked as highly reactive glycosyl acceptors of glycosyl acetates to afford aryl O-glycosides in excellent yields. A catalytic amount of ytterbium(III) trifluoromethanesulfonate activated the formation reaction of aryl O-glycosidic linka

Glycosylation of Phenols: Preparation of 1,2-cis and 1,2-trans Glycosylated Tyrosine Derivatives to be used in Solid-phase Glycopeptide Synthesis

The synthesis of four building blocks, Nα-Fmoc-Tyr(Ac4-β-D-Glc)-OPfp 6, Nα-Fmoc-Tyr(Bz4-α-D-Glc)-OPfp 16, Nα-Fmoc-Tyr4-α-D-Glc-(1->4)-Ac3-β-D-Glc>-OPfp 9 and Nα-Fmo