108836-02-8

Basic information

• Product Name: 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl bromide
• Synonyms: 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl bromide
• CAS NO: 108836-02-8
• Molecular Weight: 659.487
• Mol File: 108836-02-8.mol
• Article Data: 28

Chemical Properties

• CAS DataBase Reference: 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl bromide(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl bromide(108836-02-8)
• EPA Substance Registry System: 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl bromide(108836-02-8)

Safety Data

• Hazardous Substances Data: 108836-02-8(Hazardous Substances Data)

Upstream product

• 2592-58-7 1,2,3,4,6-penta-O-benzoyl-β-D-mannopyranose 
• 530-26-7 D-Mannose 
• 2592-58-7 1,2,3,4,6-penta-O-benzoyl-β-D-galactopyranose 
• 10257-28-0 D-Galactose 
• 98-88-4 benzoyl chloride 
• 2280-44-6 D-Glucose 
• 331455-81-3 1-p-methylphenylseleno-2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside 
• 183367-63-7 1-p-methylphenyltelluro-2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside 
• 172847-85-7 (2R,3R,4S,5R,6S)-2-((benzoyloxy)methyl)-6-(p-tolylthio)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate 
• 157896-05-4 Phenyl 2,3,4,6-tetra-O-benzoyl-1-seleno-β-D-glucopyranoside 
• 166241-68-5 ethyl 2,3,4,6-tetra-O-benzoyl-1-thio-α-D-mannopyranoside 
• 3458-28-4 D-Mannose 
• 618-32-6 Benzoyl bromide 
• 3879-79-6 (2R,3R,4S,5S,6S)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-methoxytetrahydro-2H-pyran 

Downstream Products

• 158717-30-7 (2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-(1->2)-1,3,4,6-tetra-O-acetyl-β-D-mannopyranose 
• 62774-33-8 phenyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-galactopyranoside 
• 223590-86-1 methyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->4)-2,3-di-O-benzyl-6-O-benzoyl-α-D-(4-2H)-glucopyranoside 
• 228699-81-8 methyl 2,4-di-O-acetyl-3-O-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-6-O-trityl-α-D-mannopyranoside 
• 228699-82-9 methyl 2,4-di-O-acetyl-6-O-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-3-O-trityl-α-D-mannopyranoside 
• 228699-85-2 methyl 2,4-di-O-acetyl-3-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-6-O-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-α-D-mannopyranoside 

Relevant articles and documents

Synthesis and inhibition of α-glucosidase of methyl glycyrrhetinate glycosides

The synthesis of the methyl glycyrrhetinate glycosides and inhibition of α-glucosidase were studied. The carboxyl group of glycyrrhetinic acid was methylated, and glucose and galactose were introduced into the hydroxyl group to obtain compounds 7 and 12.

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.

Regenerative Glycosylation

Previously, we communicated 3,3-difluoroxindole (HOFox)-mediated glycosylations wherein 3,3-difluoro-3H-indol-2-yl (OFox) imidates were found to be key intermediates. Both the in situ synthesis from the corresponding glycosyl bromides and activation of the OFox imidates could be conducted in a regenerative fashion. Herein, we extend this study to the synthesis of various glycosidic linkages using different sugar series. The main outcome of this study relates to enhanced yields and/or reduced reaction times of glycosylations. The effect of HOFox-mediated reactions is particularly pronounced in case of unreactive glycosyl donors and/or glycosyl acceptors. A multistep regenerative synthesis of oligosaccharides is also reported.