1464-44-4

Usage

Uses

1. Used in Pharmaceutical Industry:
PHENYL-BETA-D-GLUCOPYRANOSIDE is used as a starting material for the synthesis of various derivatives of β-D-glucopyranosides. These derivatives have potential applications as anti-HIV agents, making it a valuable compound in the development of new medications for the treatment of HIV.
2. Used in Analytical Chemistry:
PHENYL-BETA-D-GLUCOPYRANOSIDE serves as a model for glycosides in the gas phase, allowing for their spectroscopic investigation. This application aids in understanding the properties and behavior of glycosides, which are essential components of various biological molecules.
3. Used in Chromatography:
In the field of chromatography, PHENYL-BETA-D-GLUCOPYRANOSIDE is used as an internal standard in both Gas Chromatography (GC) and Gas Chromatography-Mass Spectrometry (GC-MS) quantitative analyses. Its consistent and stable properties make it an ideal reference point for accurate measurements and comparisons in these analytical techniques.

Safety Profile

Moderately toxic by intraperitoneal route. When heated to decomposition it emits acrid smoke and irritating vapors.

Purification Methods

Phenyl--D-glucopyranoside recrystallises from H2O with 2H2O and can be dried in vacuo at 100o/P2O5. The dry preparation has [] 25D -70.7o (c 2, H2O). [Robertson & Waters J Chem Soc 2729 1930, IR: Bunton et al. J Chem Soc 4419 1955, Takahashi Yakugaku Zasshi (J Pharm Soc Jpn) 74 7436 1954, Whixtler & House Anal Chem 25 1463 1953, UV: Lewis J Am Chem Soc 57 898 1935.] It is a substrate for D-glucosidase [deBryne Eur J Biochem 102 257 1979]. [Beilstein 17 III/V 2946.]

Upstream product

• 2106-10-7 1-deoxy-1-fluoro-α-D-glucose 
• 108-95-2 phenol 
• 64-17-5 ethanol 
• 75-89-8 2,2,2-trifluoroethanol 
• 4468-72-8 phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 2280-44-6 D-Glucose 
• 72366-52-0 4-phenyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 3587-18-6 tributyltin phenoxide 
• 439-03-2 2,3,4,6-tetra-O-acetyl-1-fluoro-α-D-glucopyranose 
• 133-89-1 UDP-glucose 
• 1079921-54-2 phenyl 4,6-O-(2,5-dihydroxybenzylidene)-β-D-glucopyranoside 
• 604-69-3 β-D-glucose pentaacetate 
• 83-87-4 β-D-mannopyranose pentaacetate 

Downstream Products

• 910887-45-5 phenyl-(O²,O³,O⁴-tribenzoyl-O⁶-trityl-β-D-glucopyranoside) 
• 53473-06-6 TrGlc-β-OPh 
• 910892-79-4 phenyl-(O²,O³,O⁴-triacetyl-O⁶-trityl-β-D-glucopyranoside) 
• 2169-80-4 phenyl 2,3,4,6-tetra-O-benzoyl β-D-glucopyranoside 
• 906342-20-9 phosphoric acid phenyl ester-(O¹-phenyl-β-D-glucopyranose-4,6-diyl ester) 
• 53472-79-0 phenyl-(O²,O⁴,O⁶-trimethyl-β-D-glucopyranoside) 
• 498-07-7 levoglucosan 
• 17685-05-1 phenyl β-D-glucuronide 
• 22887-10-1 phenyl 4,6-O-benzylidene-β-D-glucopyranoside 
• 97-30-3 methyl D-glucopyranoside 
• 709-50-2 methyl beta-D-glucopyranoside 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 136409-95-5 phenyl-β-D-glucopyranose-6-acetate 
• 29836-26-8 n-octyl β-D-glucopyranoside 

Relevant academic research and scientific papers

Isotope studies of the transfer of the carbon atoms of carbohydrate derivatives into aromatic compounds (especially xanthene) under degradation conditions

Treatment of various 13C-carbohydrate-labelled phenyl β-D-glucopyranosides at 350°C in aqueous phenol in the presence of zinc chloride, with 13C NMR analysis of the xanthene formed as the major neutral product, indicated that the methylene carbon atom (C-9) of this compound was derived from C-1 (30%), C-2 (20%), and C-6 (50%) of the glucosyl units. In addition, 4.5% of the carbon from the sugar was incorporated into the aromatic rings of the xanthene. Mass spectrometry of the phenol produced on heating methyl α-D-glucopyranoside (50% U-13C) at 350°C for 1 h in aqueous zinc chloride showed the aromatic rings to be derived from the glucosyl moiety, partly without cleavage of the carbon chain and also after cleavage and recombination of the fragments.

Scope of the DMC mediated glycosylation of unprotected sugars with phenols in aqueous solution

Activation of reducing sugars in aqueous solution using 2-chloro-1,3-dimethylimidazolinium chloride (DMC) and triethylamine in the presence of para-nitrophenol allows direct stereoselective conversion to the corresponding 1,2-Trans para-nitrophenyl glycosides without the need for any protecting groups. The reaction is applicable to sulfated and phosphorylated sugars, but not to ketoses or uronic acids or their derivatives. When applied to other phenols the product yield was found to depend on the pKa of the added phenol, and the process was less widely applicable to 2-Acetamido sugars. For 2-Acetamido substrates an alternative procedure in which the glycosyl oxazoline was pre-formed, the reaction mixture freeze-dried, and the crude product then reacted with an added phenol in a polar aprotic solvent system with microwave irradiation proved to be a useful simplification.

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)).

Deacetylation of per-acetatylated glycopyranosides: An overall pattern for acidic catalyzis

Acetyl protecting groups are commonly used in carbohydrate chemistry. Partially acetylated arylglycosides are not only useful building blocks in syntheses, but they are also substantial for plant metabolism. Nonselective base catalysis is often used for removing the acetyl groups. Even though acid-catalyzed deacetylation might be more selective, it is seldom used in carbohydrate chemistry, because it has not been thoroughly investigated. In this work, we study the acid-catalyzed deacetylation of per-acetylated phenyl glycosides experimentally and computationally by using density functional theory (DFT) calculations. Based on quantum modeling, we design a general scheme for the stepwise acid-catalyzed deacetylation of arylglycosides per-acetates. The approach can also be applied on gluco- and galactopyranosides. We have studied the deacetylation reaction in solvents of different polarity and found that the activation barriers of the stepwise deacetylation mechanism increase with increasing polarity of the solvent.

A new look at acid catalyzed deacetylation of carbohydrates: A regioselective synthesis and reactivity of 2-O-acetyl aryl glycopyranosides

In the present work we report that acetyl groups of per – acetylated aryl glycosides have different reactivity during the acidic deacetylation using HCl/EtOH in CHCl3, which leads to preferential deacetylation at O-3, O-4 and O-6. Thereby, the one-step preparation of 2-O-acetyl aryl glycosides with simple aglycon was accomplished for the first time. It was proved that the found reagent is to be general and unique for the preparation of series of 2-О-acetyl aryl glycosides. We have determined the influence of both carbohydrate moiety and the aglycon on the selectivity of deacetylation reaction by kinetic experiments. Using DFT/B3LYP/6-31G(d,p) and semi-empirical АМ1 methods we have found that the highest activation barrier is for 2-О-acetyl group. This completely explains the least reactivity of 2-О-acetyl group.

Rapid phenolic O-glycosylation of small molecules and complex unprotected peptides in aqueous solvent

Glycosylated natural products and synthetic glycopeptides represent a significant and growing source of biochemical probes and therapeutic agents. However, methods that enable the aqueous glycosylation of endogenous amino acid functionality in peptides without the use of protecting groups are scarce. Here, we report a transformation that facilitates the efficient aqueous O-glycosylation of phenolic functionality in a wide range of small molecules, unprotected tyrosine, and tyrosine residues embedded within a range of complex, fully unprotected peptides. The transformation, which uses glycosyl fluoride donors and is promoted by Ca(OH)2, proceeds rapidly at room temperature in water, with good yields and selective formation of unique anomeric products depending on the stereochemistry of the glycosyl donor. High functional group tolerance is observed, and the phenol glycosylation occurs selectively in the presence of virtually all side chains of the proteinogenic amino acids with the singular exception of Cys. This method offers a highly selective, efficient, and operationally simple approach for the protecting-group-free synthesis of O-aryl glycosides and Tyr-O-glycosylated peptides in water.

PHENOL GLYCOSIDES AND THEIR USE IN THE TREATMENT OF UROLITHIASIS

The present invention relates to novel derivatives of polyphenol glycoside or polyalcohols of formula (1), wherein R1, R2, R3 is selected from the group consisting of H, OH, C(O)R4, C(0) OR4, 0 (Gly H3)n, wherein n = 0 1, 2, 3, and R4 is selected from the group consisting of H, alkyl, and Gly is a mono- or disaccharide residue. The present invention also relates to novel derivatives of glycoside polyphenols or polyalcohols, as pharmaceutical composition comprising a novel polyphenol glycoside or polyalcohols and the use of novel polyphenol glycoside or polyalcohols for the treatment of urolithiasis.

Selective C?O Bond Cleavage of Sugars with Hydrosilanes Catalyzed by Piers’ Borane Generated In Situ

Described herein is the selective reduction of sugars with hydrosilanes catalyzed by using Piers’ borane [(C6F5)2BH] generated in situ. The hydrosilylative C?O bond cleavage of silyl-protected mono- and disaccharides in the presence of a (C6F5)2BH catalyst, generated in situ from (C6F5)2BOH, takes place with excellent chemo- and regioselectivities to provide a range of polyols. A study of the substituent effects of sugars on the catalytic activity and selectivity revealed that the steric environment around the anomeric carbon (C1) is crucial.

COMPOUNDS AND METHODS FOR TREATING BACTERIAL INFECTIONS

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

FimH antagonists for the oral treatment of urinary tract infections: From design and synthesis to in vitro and in vivo evaluation

Urinary tract infection (UTI) by uropathogenic Escherichia coli (UPEC) is one of the most common infections, particularly affecting women. The interaction of FimH, a lectin located at the tip of bacterial pili, with high mannose structures is critical for the ability of UPEC to colonize and invade the bladder epithelium. We describe the synthesis and the in vitro/in vivo evaluation of α-d-mannosides with the ability to block the bacteria/host cell interaction. According to the pharmacokinetic properties, a prodrug approach for their evaluation in the UTI mouse model was explored. As a result, an orally available, low molecular weight FimH antagonist was identified with the potential to reduce the colony forming units (CFU) in the urine by 2 orders of magnitude and in the bladder by 4 orders of magnitude. With FimH antagonist 16b, the great potential for the effective treatment of urinary tract infections with a new class of orally available antiinfectives could be demonstrated.