14581-80-7

Basic information

• Product Name: 4-bromophenyl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside
• Synonyms: b-D-Glucopyranoside, 4-bromophenyl tetraacetate
• CAS NO: 14581-80-7
• Molecular Formula: C₂₀H₂₃BrO₁₀
• Molecular Weight: 503.2946
• Mol File: 14581-80-7.mol

Chemical Properties

• Boiling Point: 529.586°C at 760 mmHg
• Flash Point: 274.084°C
• Density: 1.479g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.548
• CAS DataBase Reference: 4-bromophenyl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: 4-bromophenyl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside(14581-80-7)
• EPA Substance Registry System: 4-bromophenyl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside(14581-80-7)

Safety Data

• Hazardous Substances Data: 14581-80-7(Hazardous Substances Data)

Upstream product

• 106-41-2 4-bromo-phenol 
• 604-69-3 β-D-glucose pentaacetate 
• 17878-44-3 (4-bromophenoxy)trimethylsilane 
• 604-68-2 α-D-glucopyranose peracetylate 
• 4468-72-8 phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 3947-62-4 2,3,4,5-tetra-O-acetyl-D-glucopyranose 
• 5467-74-3 4-Bromophenylboronic acid 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 439-03-2 2,3,4,6-tetra-O-acetyl-1-fluoro-α-D-glucopyranose 

Downstream Products

• 1053261-43-0 Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-(4'-decyloxy-3'-fluoro-biphenyl-4-yloxy)-tetrahydro-pyran-3-yl ester 
• 1053645-59-2 Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-(4'-propylsulfanyl-biphenyl-4-yloxy)-tetrahydro-pyran-3-yl ester 
• 30572-42-0 4-bromophenyl-β-D-glucopyranoside 

Relevant articles and documents

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.

Antagonists of the myelin-associated glycoprotein: A new class of tetrasaccharide mimics

The tetrasaccharide substructure 1 of the ganglioside GQ1bα shows a remarkable affinity for the myelin-associated glycoprotein (MAG). In the search for structurally simplified and pharmacokinetically improved mimics of 1, biphenyl was identified as a feas

Synthesis of carbohydrate functionalised n-propoxy-Calix[4]arenes

The Suzuki reaction has been used to couple para-bromophenyl glycosides to boronic acid derivatives of n-propoxy-Calix[4]arene; 'a one-pot' methodology eliminates the need to isolate the boronic acids and increases the overall yield. The synthesis provides a new class of carbohydrate containing calixarenes with a deepened cavity.

Regioselective Bromination of O-β-Glycosylated Aromatics

The quasi quantitative and regioselective bromination of O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)phenols is described.The orientating effect of the glycoside group is compared with those of other oxygenated groups and its usefulness illustrated with

A New Approach to Carbohydrate Functionalized Aromatic Compounds

Liquid crystalline aryl-β-O-D-glucosides are synthesized by palladium-catalysed cross-coupling of 4-bromophenyl-β-O-D-tetraacetylglucoside with boronic acids.

Glycosides. Part 1. New Synthesis of 1,2-trans O-Aryl Glycosides, via Tributyltin Phenoxides

A new method of glycosidation of phenols has been studied.The reaction of tributyltin phenoxides 2 with 1,2,3,4,6-penta-O-acetyl-D-hexopyranosides 3, 7 and 9, in the presence of tin tetrachloride is described.Glycosides 4, 8 and 10 have been isolated in g

Novel Synthesis of Aryl 2,3,4,6-Tetra-O-acetyl-D-glucopyranosides

The glucosidation of phenols with 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl fluoride in the presence of BF3*OEt2 to give, predominantly, α-anomers has been studied.In the presence of an amine base, 1,1,3,3-tetramethylguanidine, however, enhanced β-selectivity was achieved.The former reaction provides a novel and useful synthesis of aryl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside whilst the latter is effective for the glycosidation of relatively hindered phenols.