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 
• 3879-79-6 methyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 73630-93-0 1-bromo-N,N,2-trimethyl-1-propen-1-amine 
• 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 
• 131531-76-5 p-methylphenyl 2,3,4,6-tetra-O-benzyl-thio-β-D-glucopyranoside 
• 1152-39-2 p-methylphenyl 1-thio-β-D-glucopyranoside 
• 28244-94-2 4-methylphenyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside 
• 131531-70-9 4-methylphenyl 2,3,4,6-tetra-O-benzyl-1-thio-α-D-mannopyranoside 
• 125411-99-6 ethyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside 
• 3866-62-4 2,3,4,6-tetra-O-benzyl-D-galactopyranosyl acetate 
• 74666-83-4 S-ethyl 2,3,4,6-tetra-O-benzyl-1-deoxy-1-thio-α-D-mannopyranoside 

Downstream Products

• 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 
• 4132-26-7 1,5-anhydro-2,3,4,6-tetra-O-benzyl-D-arabino-hex-1-enitol 
• 112219-64-4 (2R,3R,4R,5S,6S)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-phenyltetrahydro-2H-pyran 
• 56632-55-4 cyclohexyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 
• 56632-56-5 cyclohexyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside 
• 104056-93-1 (3β,5β,14β,17β)-3-<(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)oxy>-14-hydroxycard-20(22)-enolide 

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.

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.

β-Selective C-Glycosylation and its Application in the Synthesis of Scleropentaside A

C-Glycosides are carbohydrates that bear a C?C bond to an aglycon at the anomeric center. Due to their high stability towards chemical and enzymatic hydrolysis, these compounds are widely used as carbohydrate mimics in drug development. Herein, we report a general and exclusively β-selective method for the synthesis of a naturally abundant acyl-C-glycosidic structural motif first found in the scleropentaside natural product family. A Corey–Seebach umpolung reaction as the key step in the synthesis of scleropentaside A and analogues enables the β-selective construction of the anomeric C?C bond starting from unprotected carbohydrates in only four steps. The one-pot approach is highly atom-efficient and avoids the use of toxic heavy metals.