4756-30-3

Basic information

• Product Name: 4'-CHLOROPHENYL-BETA-D-GLUCOPYRANOSIDE
• Synonyms: 4'-CHLOROPHENYL-BETA-D-GLUCOPYRANOSIDE;4-Chlorophenylb-D-glucopyranoside;4''-CHLOROPHENYL-SS-D-GLUCOPYRANOSIDE;4-Chlorophenyl-β-D-glucopyranoside;p-Chlorophenyl beta-D-glucoside;p-Chlorophenylbeta-D-glucopyranoside;b-D-Glucopyranoside, 4-chlorophenyl-
• CAS NO: 4756-30-3
• Molecular Formula: C₁₂H₁₅ClO₆
• Molecular Weight: 290.6969
• EINECS: 1533716-785-6
• Mol File: 4756-30-3.mol
• Article Data: 2

Chemical Properties

• Melting Point: 179-180℃
• Boiling Point: 510℃
• Flash Point: 263℃
• Appearance: /
• Density: 1.542
• PKA: 12.75±0.70(Predicted)
• CAS DataBase Reference: 4'-CHLOROPHENYL-BETA-D-GLUCOPYRANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4'-CHLOROPHENYL-BETA-D-GLUCOPYRANOSIDE(4756-30-3)
• EPA Substance Registry System: 4'-CHLOROPHENYL-BETA-D-GLUCOPYRANOSIDE(4756-30-3)

Safety Data

• Hazardous Substances Data: 4756-30-3(Hazardous Substances Data)

Usage

General Description

"4'-Chlorophenyl-beta-D-glucopyranoside" is a chemical compound with the molecular formula C12H15ClO7. It is a derivative of beta-D-glucopyranoside with a 4'-chlorophenyl group attached to the sugar molecule. 4'-CHLOROPHENYL-BETA-D-GLUCOPYRANOSIDE is often used in research and pharmaceutical applications as a substrate for enzymes involved in sugar metabolism. It is also used as a reference standard for analytical methods, particularly in the field of carbohydrate chemistry. The presence of the chlorophenyl group makes it useful for studying the reactivity and selectivity of various enzymes and chemical reactions. Additionally, it has potential applications in drug development and medicinal chemistry due to its ability to interact with biological systems.

Upstream product

• 5041-92-9 p-chlorophenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 106-48-9 4-chloro-phenol 
• 2106-10-7 1-deoxy-1-fluoro-α-D-glucose 

Downstream Products

• 24573-38-4 4-chlorophenolate 
• 2280-44-6 D-Glucose 
• 106-48-9 4-chloro-phenol 
• 107807-32-9 p-chlorophenyl 2-O-β-D-mannopyranosyl-β-D-mannopyranoside 
• 107807-31-8 p-chlorophenyl 6-O-β-D-mannopyranosyl-β-D-mannopyranoside 

Relevant articles and documents

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.