131897-73-9

Basic information

• Product Name: 2,3,4-tri-O-benzoylfucopyranosyl bromide
• Synonyms: 2,3,4-tri-O-benzoylfucopyranosyl bromide
• CAS NO: 131897-73-9
• Molecular Formula: C₂₇H₂₃BrO₇
• Molecular Weight: 0
• Mol File: 131897-73-9.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 621.9°C at 760 mmHg
• Flash Point: 329.9°C
• Appearance: /
• Density: 1.46g/cm³
• Vapor Pressure: 2.18E-15mmHg at 25°C
• Refractive Index: 1.628
• CAS DataBase Reference: 2,3,4-tri-O-benzoylfucopyranosyl bromide(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4-tri-O-benzoylfucopyranosyl bromide(131897-73-9)
• EPA Substance Registry System: 2,3,4-tri-O-benzoylfucopyranosyl bromide(131897-73-9)

Safety Data

• Hazardous Substances Data: 131897-73-9(Hazardous Substances Data)

Usage

General Description

2,3,4-tri-O-benzoylfucopyranosyl bromide is a chemical compound with the molecular formula C21H19BrO8. It is a derivative of fucose, a monosaccharide sugar, and is commonly used as a reagent in organic synthesis and carbohydrate chemistry. 2,3,4-tri-O-benzoylfucopyranosyl bromide is a highly reactive bromide derivative that is often utilized in the synthesis of complex carbohydrates and glycoconjugates. Its high reactivity allows for efficient and selective glycosylation reactions, making it a valuable tool in the creation of various glycoconjugates and glycans for research and industrial applications. Due to its potential as a versatile building block in carbohydrate chemistry, 2,3,4-tri-O-benzoylfucopyranosyl bromide is of significant interest to chemists and researchers working in the field of carbohydrate synthesis and glycochemistry.

InChI:InChI=1/C27H23BrO7/c1-17-21(33-25(29)18-11-5-2-6-12-18)22(34-26(30)19-13-7-3-8-14-19)23(24(28)32-17)35-27(31)20-15-9-4-10-16-20/h2-17,21-24H,1H3/t17-,21+,22+,23-,24+/m0/s1

Upstream product

• 61198-83-2 1,2,3,4-tetra-O-benzoyl-6-desoxy-α-L-mannopyranose 
• 84635-55-2 methyl 2,3,4-tri-O-acetyl-1-thio-α-L-rhamnopyranoside 
• 115678-08-5 methyl 1-thio-α-L-rhamnopyranoside 
• 98-88-4 benzoyl chloride 
• 7404-35-5 1,2,3,4-tetra-O-acetyl-L-rhamnopyranose 
• 115678-19-8 methyl 2,3,4-tri-O-benzoyl-1-thio-α-L-rhamnopyranoside 
• 73-34-7 6-deoxy-L-galactose 
• 135266-93-2 1,2,3,4-tetra-O-benzoyl-α-L-fucopyranoside 
• 140223-15-0 (3S,4R,5R,6S)-6-methyltetrahydro-2H-pyran-2,3,4,5-tetrayl tetrabenzoate 
• 180581-28-6 2,3,4-tri-O-benzoyl-L-fucopyranose 
• 73-34-7 L-rhamnose 
• 3615-41-6 L-Rhamnose 
• 6155-35-7 L-rhamnose monohydrate 

Downstream Products

• 137438-99-4 Methyl 2-O-acetyl-4-O-benzyl-3-O-(2,3,4-tri-O-benzoyl-β-L-fucopyranosyl)-α-L-rhamnopyranoside 
• 137439-01-1 Methyl 2-O-acetyl-4-O-benzyl-3-O-(2,3,4-tri-O-benzoyl-α-L-fucopyranosyl)-α-L-rhamnopyranoside 
• 135129-62-3 Methyl 3,4-di-O-benzoyl-2-O-(2,3,4-tri-O-benzoyl-α-L-fucopyranosyl)-α-L-rhamnopyranoside 
• 137439-13-5 1,3,4-tri-O-benzoyl-α-L-fucopyranose 
• 137439-07-7 C₄₉H₅₀O₁₃ 
• 137439-03-3 Methyl 4-O-benzoyl-3-O-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-2-O-(2,3,4-tri-O-benzoyl-α-L-fucopyranosyl)-α-L-rhamnopyranoside 
• 138552-47-3 dibenzyl 2,3,4-tri-O-benzoyl-β-L-fucopyranosyl 1-phosphate 

Relevant articles and documents

Synthesis of Glycosyl Chlorides and Bromides by Chelation Assisted Activation of Picolinic Esters under Mild Neutral Conditions

A general method has been developed for the formation of glycosyl chlorides and bromides from picolinic esters under mild and neutral conditions. Benchtop stable picolinic esters are activated by a copper(II) halide species to afford the corresponding products in high yields with a traceless leaving group. Rare β glycosyl chlorides are accessible via this route through neighboring group participation. Additionally, glycosyl chlorides with labile protecting groups previously not easily accessible can be prepared.

Stereoselective Epimerizations of Glycosyl Thiols

Glycosyl thiols are widely used in stereoselective S-glycoside synthesis. Their epimerization from 1,2-trans to 1,2-cis thiols (e.g., equatorial to axial epimerization in thioglucopyranose) was attained using TiCl4, while SnCl4 promoted their axial-to-equatorial epimerization. The method included application for stereoselective β-d-manno- and β-l-rhamnopyranosyl thiol formation. Complex formation explains the equatorial preference when using SnCl4, whereas TiCl4 can shift the equilibrium toward the 1,2-cis thiol via 1,3-oxathiolane formation.

Fast and efficient preparation of an α-fucosyl building block by reductive 1,2-benzylidene ring-opening reaction

1,2-Benzylidene ring opening on fucose was promoted in the presence of different reducing agents and Lewis acids, providing a fast access to fucosyl building blocks.