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

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

Used in Organic Synthesis:
2,3,4,6-Tetra-O-benzyl-α-D-glucopyranosyl bromide is used as a synthetic intermediate for the preparation of various complex organic compounds. Its unique structure allows for selective reactions and functional group manipulations, making it a valuable building block in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Carbohydrate Chemistry:
In the field of carbohydrate chemistry, 2,3,4,6-Tetra-O-benzyl-α-D-glucopyranosyl bromide is used as a glycosyl donor for the synthesis of oligosaccharides and glycoconjugates. Its benzyl protecting groups can be selectively removed to facilitate the formation of glycosidic bonds, enabling the construction of complex carbohydrate structures.
Used in Glycoprotein Synthesis:
2,3,4,6-Tetra-O-benzyl-α-D-glucopyranosyl bromide is used as a precursor to prepare glycosyl phenylthiosulfonates (Glyco-PTS), which are novel reagents for glycoprotein synthesis. These reagents offer advantages such as high reactivity, mild reaction conditions, and compatibility with various protecting group strategies, making them valuable tools for the preparation of biologically relevant glycoproteins.
Used in Pharmaceutical Industry:
2,3,4,6-Tetra-O-benzyl-α-D-glucopyranosyl bromide is used as a key intermediate in the synthesis of glycoconjugate drugs, which are a class of pharmaceuticals that incorporate carbohydrate moieties into their structures. These drugs often exhibit improved pharmacokinetic properties, enhanced solubility, and increased stability compared to their non-glycosylated counterparts.
Used in Agrochemical Industry:
In the agrochemical industry, 2,3,4,6-Tetra-O-benzyl-α-D-glucopyranosyl bromide is used as a building block for the synthesis of glycosylated agrochemicals, such as pesticides and herbicides. The introduction of carbohydrate moieties can improve the solubility, bioavailability, and environmental compatibility of these compounds, leading to more effective and sustainable agricultural products.

Upstream product

• 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 
• 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 
• 2280-44-6 D-Glucose 
• 182074-52-8 pent-4-enyl α,β-D-glucopyranoside 
• 15219-34-8 Oxalyl bromide 

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.

Chemical glucosylation of pyridoxine

The chemical synthesis of pyridoxine-5′-β-D-glucoside (5′-β-PNG) was investigated using various glucoside donors and promoters. Hereby, the combination of α4,3-O-isopropylidene pyridoxine, glucose vested with different leaving and protecting groups and the application of stoichiometric amounts of different promoters was examined with regards to the preparation of the twofold protected PNG. Best results were obtained with 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl fluoride and boron trifluoride etherate (2.0 eq.) as promoter at 0 °C (59%). The deprotection was accomplished stepwise with potassium/sodium hydroxide in acetonitrile/water followed by acid hydrolysis with formic acid resulting in the chemical synthesis of 5′-β-PNG.

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.

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.

Establishment of Guidelines for the Control of Glycosylation Reactions and Intermediates by Quantitative Assessment of Reactivity

Stereocontrolled chemical glycosylation remains a major challenge despite vast efforts reported over many decades and so far still mainly relies on trial and error. Now it is shown that the relative reactivity value (RRV) of thioglycosides is an indicator for revealing stereoselectivities according to four types of acceptors. Mechanistic studies show that the reaction is dominated by two distinct intermediates: glycosyl triflates and glycosyl halides from N-halosuccinimide (NXS)/TfOH. The formation of glycosyl halide is highly correlated with the production of α-glycoside. These findings enable glycosylation reactions to be foreseen by using RRVs as an α/β-selectivity indicator and guidelines and rules to be developed for stereocontrolled glycosylation.

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.

β-Selective One-Pot Synthesis of Acyl-C-Glycosides via Corey-Seebach Umpolung Reaction

C-Glycosides are commonly used as carbohydrate mimics in drug development due to their stability against enzymatic and chemical hydrolysis. In this Synpacts article we elaborate on our fast and efficient β-selective approach towards protected and unprotected acyl glycosides. Application of a Corey-Seebach umpolung reaction enables the exclusive formation of the β-Anomer of aromatic acyl-C-glycosides in good to excellent yields. 1 Introduction 2 C-Glycosylation of Benzylated Glycosyl Donors 3 C-Glycosylation of Silylated Glycosyl Donors 4 Conclusion.

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.

Method for synthesizing ipragliflozin

The invention discloses a method for synthesizing ipragliflozin. The method comprises the following steps: (1) generating alkylation reaction by formula-4 compound and formula-5 compound to generate aformula-6 compound; (2) carrying out deprotection on the formula-6 compound to generate a formula-7 compound, i.e., ipragliflozin. Compared with the prior art, the preparation method disclosed by theinvention is characterized in that adopted starting raw materials are cheap and can be easily obtained, a synthesis route is short, operation is convenient, cost is lower and general yield is high. The method conforms to the concept of green chemistry and is suitable for industrial production. (The formulas are shown in the description.).

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.