2818-58-8

Basic information

• Product Name: Phenylgalactoside
• Synonyms: beta-d-galactopyranoside,phenyl;p-gal;PH-BETA-D-GAL;phenylgalactoside;PHENYL-B-D-GALACTOPYRANOSIDE;PHENYL-BETA-D-GALACTOPYRANOSIDE;PHENYL-BETA-D-GALACTOSIDE;PHENYL-BETA-D-GALATOPYRANOSIDE
• CAS NO: 2818-58-8
• Molecular Formula: C₁₂H₁₆O₆
• Molecular Weight: 256.25
• EINECS: 220-573-2
• Product Categories: Sugars, Carbohydrates & Glucosides;Biochemistry;Galactose;Glycosides;Sugars;substrate
• Mol File: 2818-58-8.mol
• Article Data: 9

Chemical Properties

• Melting Point: 153-155 °C(lit.)
• Boiling Point: 359.49°C (rough estimate)
• Flash Point: 245.4 °C
• Appearance: white powder
• Density: 1.2993 (rough estimate)
• Vapor Pressure: 4.17E-10mmHg at 25°C
• Refractive Index: -42 ° (C=2.3, H2O)
• Storage Temp.: 2-8°C
• PKA: 12.70±0.70(Predicted)
• Water Solubility: very faint turbidity in Water
• Stability: Stable. Incompatible with strong oxidizing agents.
• BRN: 87518
• CAS DataBase Reference: Phenylgalactoside(CAS DataBase Reference)
• NIST Chemistry Reference: Phenylgalactoside(2818-58-8)
• EPA Substance Registry System: Phenylgalactoside(2818-58-8)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• F: 3-10-21
• Hazardous Substances Data: 2818-58-8(Hazardous Substances Data)

Usage

Chemical Properties

white powder

Purification Methods

Recrystallisation of phenyl--D-galactopyranoside from H2O gives the 0.5H2O. [Conchie & Hay Biochem J 73 327 1959, IR: Whistler & House Analyt Chem 25 1463 1953.] It is an acceptor substrate for fucosyltransferase [Chester et al. Eur J Biochem 69 583 1976]. [Beilstein 17/7 V46.]

InChI:InChI=1/C12H16O6/c13-6-8-9(14)10(15)11(16)12(18-8)17-7-4-2-1-3-5-7/h1-5,8-16H,6H2/t8-,9+,10+,11-,12-/m1/s1

Upstream product

• 108-95-2 phenol 
• 4163-60-4 β-D-galactose peracetate 
• 3068-32-4 1-bromo-2,3,4,6-tetra-O-acetyl-D-galactopyranose 
• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 
• 25878-60-8 D-galactose pentaacetate 
• 2872-72-2 phenyl-2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside 
• 1259428-56-2 phenyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranoside 
• 83-87-4 β-D-mannopyranose pentaacetate 
• 83-87-4 D-Mannose pentaacetate 
• 2872-72-2 phenyl α-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 

Downstream Products

• 117677-62-0 phenyl 4,6-O-(S)-benzylidene-β-D-galactopyranoside 
• 185754-29-4 phenyl 4,6-O-para-methoxybenzylidene-β-D-galactopyranoside 
• 34213-07-5 phenyl 2,3,6-tri-O-benzoyl-β-D-galactopyranoside 
• 878806-10-1 phenyl (S)-2,3:4,6-O-di-benzylidene-α-D-mannopyranoside 
• 878806-18-9 phenyl 6-O-trityl-α-D-mannopyranoside 
• 878806-06-5 phenyl 2-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside 
• 878806-21-4 phenyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl-(1->3)-α-D-mannopyranoside 
• 878806-19-0 phenyl 2,3,4-tri-O-benzyl-6-O-trityl-α-D-mannopyranoside 
• 878806-04-3 phenyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl-(1->3)-2-O-benzyl-4,6-benzylidene-α-D-mannopyranoside 
• 357187-42-9 phenyl 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannopyranoside 
• 849938-02-9 phenyl 2,3,4-tri-O-benzyl-α-D-mannopyranoside 

Relevant articles and documents

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)).

Stereocontrolled Synthesis of Phenolic α-d-Glycopyranosides

Adopting the ‘remote activation concept’ toward stereocontrolled glycoside synthesis with minimal use of protection groups, a general synthesis of phenolic 1,2-cis glycopyranosides is reported, as exemplified by aryl α-d-galacto-, α-d-gluco- and 2-azido α-d-glucopyranosides among others using glycosyl donors bearing an anomeric (3-bromo-2-pyridyloxy) group and catalyzed by methyl triflate.

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.