4196-35-4

Basic information

• Product Name: 2,3,4,6-Tetra-O-benzyl-a-D-glucopyranosylbromide
• Synonyms: 2,3,4,6-Tetra-O-benzyl-a-D-glucopyranosylbromide;(2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-2-bromo-6-(3-phenylpropyl)tetrahydro-2H-pyran;(2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-2-broMo-6-(3-phenylpropyl;2,3,4,6-Tetra-O-benzyl-α-D-glucopyranosyl BroMide;2,3,4,6-Tetra-O-benzyl-1-bromo-1-deoxy-alpha-D-glucopyranose;2,3,4,6-Tetra-O-benzyl-alpha-D-bromoglucopyranoside;2,3,4,6-Tetra-O-benzyl-alpha-D-glucopyranosyl bromide
• CAS NO: 4196-35-4
• Molecular Formula: C₃₄H₃₅BrO₅
• Molecular Weight: 603.54
• Mol File: 4196-35-4.mol
• Article Data: 60

Chemical Properties

• Boiling Point: 667.1±55.0 °C(Predicted)
• Appearance: /
• Density: 1.31±0.1 g/cm3(Predicted)
• Storage Temp.: Hygroscopic, -86°C Freezer, Under inert atmosphere
• Solubility: Chloroform (Slightly), Dichloromethane (Slightly), Ethyl Acetate (Slightly)
• Stability: Hygroscopic, Moisture Sensitive, Temperature Sensitive
• CAS DataBase Reference: 2,3,4,6-Tetra-O-benzyl-a-D-glucopyranosylbromide(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4,6-Tetra-O-benzyl-a-D-glucopyranosylbromide(4196-35-4)
• EPA Substance Registry System: 2,3,4,6-Tetra-O-benzyl-a-D-glucopyranosylbromide(4196-35-4)

Safety Data

• Hazardous Substances Data: 4196-35-4(Hazardous Substances Data)

Usage

Uses

2,3,4,6-Tetra-O-benzyl-α-D-glucopyranosyl Bromide is a useful synthetic intermediate. It can be used to prepare glycosyl phenylthiosulfonates (Glyco-PTS), a novel reagents for glycoprotein synthesis. It is also used to synthesize oligosaccharides.

Upstream product

• 80300-30-7 1-O-acetyl-2,3,4,6-tetra-O-benzyl-D-glucopyranose 
• 4196-36-5 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl 4-nitrobenzoate 
• 74666-83-4 1-deoxy-1-(S-ethyl)-2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside 
• 74666-83-4 ethyl 2-O-benzoyl-3,4,6-tri-O-benzyl-1-thio-α-D-glucopyranoside 
• 6564-72-3 2,3,4,6-tetra-O-benzyl-D-glucopyranose 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 104992-64-5 methyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranoside 
• 30608-21-0 1-O-trimethylsilyl-2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 
• 78153-79-4 2,3,4,6-tetra-O-benzyl-D-glucopyranosyl fluoride 
• 134003-35-3 pent-4-enyl 2,3,4,6-tetra-O-benzyl-D-glucopyranoside 
• 54423-54-0 2,3,4,6-Tetra-O-benzyl 1-O-p-nitrobenzoyl D-glucopyranoside 
• 95058-04-1 2,3,4,6-tetra-O-benzyl-1-O-p-nitrobenzyl-α-D-glucopyranose 
• 59531-24-7 2,3,4,6-tetra-O-benzyl-D-glucopyranoside 
• 3879-79-6 methyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 

Downstream Products

• 74279-34-8 7-(tetra-O-benzyl-β-D-glucopyranosyloxy)-10H-dibenzo[b,f][1,4]oxazepin-11-one 
• 74256-85-2 4-(tetra-O-benzyl-β-D-glucopyranosyloxy)-10H-dibenzo[b,f][1,4]oxazepin-11-one 
• 77895-19-3 2,2,6,6-tetramethylpiperidin-4-yl tetra-O-benzyl-α-D-glucopyranoside hydrobromide 
• 130656-21-2 benzyl 2-acetamido-3,6-di-O-acetyl-2-deoxy-4-O-(2,3,4,6-tetra-O-benzyl-α/β-D-glucopyranosyl)-α-D-glucopyranoside 
• 130656-24-5 2,4,6-trimethyl-1-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)pyridinium chloride 
• 130656-23-4 2,4,6-trimethyl-1-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)pyridinium chloride 
• 130656-26-7 2,4,6-trimethyl-1-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)pyridinium bromide 
• 130656-25-6 2,4,6-trimethyl-1-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)pyridinium bromide 
• 108739-68-0 methyl O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-β-D-glucopyranoside 
• 101068-06-8 methyl 4,6-O-benzylidene-3-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-α-D-glucopyranoside 
• 101125-96-6 methyl 4,6-O-benzylidene-2-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-β-D-glucopyranoside 
• 101068-07-9 methyl 4,6-O-benzylidene-3-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-β-D-glucopyranoside 
• 55094-26-3 methyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl-(1-6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 56632-57-6 methyl O-2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->6)-2,3,4-tri-O-benzyll-α-D-glucopyranoside 

Relevant articles and documents

Halide-mediated regioselective 6-O-glycosylation of unprotected hexopyranosides with perbenzylated glycosyl bromide donors

The regio- and stereoselective glycosylation at the 6-position in 2,3,4,6-unprotected hexopyranosides has been investigated with dibutyltin oxide as the directing agent. Perbenzylated hexopyranosyl bromides were employed as the donors and the glycosylations were promoted by tetrabutylammonium bromide. The couplings were completely selective for both glucose and galactose donors and acceptors as long as the stannylene acetal of the acceptor was soluble in dichloromethane. This gave rise to a number of 1,2-cis-linked disaccharides in reasonable yields. Mannose donors and acceptors, on the other hand, did not react in the glycosylation under these conditions.

Indolylthio glycosides as effective building blocks for chemical glycosylation

The S-indolyl (SIn) anomeric moiety was investigated as a new leaving group that can be activated for chemical glycosylation under a variety of conditions including thiophilic and metal-assisted pathways. Understanding of the reaction pathways for the SIn moiety activation was achieved via the extended mechanistic study. Also reported is how the new SIn donors fit into selective activation strategies for oligosaccharide synthesis.

Koenigs–Knorr Glycosylation Reaction Catalyzed by Trimethylsilyl Trifluoromethanesulfonate

The discovery that traditional silver(I)-oxide-promoted glycosidations of glycosyl bromides (Koenigs–Knorr reaction) can be greatly accelerated in the presence of catalytic trimethylsilyl trifluoromethanesulfonate (TMSOTf) is reported. The reaction conditions are very mild that allowed for maintaining a practically neutral pH and, at the same time, providing high rates and excellent glycosylation yields. In addition, unusual reactivity trends among a series of differentially protected glycosyl bromides were documented. In particular, benzoylated α-bromides were much more reactive than their benzylated counterparts under these conditions.