64768-20-3

Usage

Uses

Used in Pharmaceutical Industry:
2,3,4,6-TETRA-O-BENZYL-D-GLUCOPYRANOSE is used as a chiral building block for the synthesis of saponins and glycosides, which are important compounds in the development of pharmaceuticals. These compounds have various biological activities, such as anti-inflammatory, antifungal, and antiviral properties, making them valuable for the treatment of various diseases and conditions.
Used in Organic Synthesis:
2,3,4,6-TETRA-O-BENZYL-D-GLUCOPYRANOSE is also used as a versatile intermediate in organic synthesis. Its unique structure allows for various chemical reactions, such as glycosylation, to be performed, enabling the synthesis of a wide range of complex organic molecules with potential applications in various fields, including medicine, agriculture, and materials science.
Used in Research and Development:
2,3,4,6-TETRA-O-BENZYL-D-GLUCOPYRANOSE serves as a valuable tool in research and development, particularly in the field of carbohydrate chemistry. Its unique properties and reactivity make it an ideal candidate for studying the structure, function, and interactions of carbohydrates, which can lead to a better understanding of their role in biological systems and the development of new therapeutic agents.

InChI:InChI=1/C34H28O10/c35-30(22-13-5-1-6-14-22)40-21-26-27(42-31(36)23-15-7-2-8-16-23)28(43-32(37)24-17-9-3-10-18-24)29(34(39)41-26)44-33(38)25-19-11-4-12-20-25/h1-20,26-29,34,39H,21H2/t26-,27-,28+,29-,34u/m1/s1

Upstream product

• 2592-58-7 1,2,3,4,6-penta-O-benzoyl-α-D-mannopyranoside 
• 2592-58-7 1,2,3,4,6-penta-O-benzoyl-β-D-mannopyranose 
• 22415-91-4 1,2,3,4,6-penta-O-benzoyl-α-D-glucopyranose 
• 2592-58-7 1,2,3,4,6-penta-O-benzoyl-β-D-glucopyranose 
• 492-62-6 alpha-D-glucopyranose 
• 7464-56-4 1-O-allyl-α-D-glucopyranoside 
• 1435780-53-2 allyl 2,3,4,6-tetra-O-benzoyl-α-D-glucopyranoside 
• 98-88-4 benzoyl chloride 
• 97590-76-6 benzyl-O-β-D-glucopyranoside 
• 18685-18-2 3-O-benzyl-1,2-5,6-O-diisopropylidene-α-D-glucofuranose 
• 100-44-7 benzyl chloride 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 492-61-5 β-D-glucose 
• 105376-04-3 ethyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-glucopyranoside 

Downstream Products

• 14726-07-9 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl iodide 
• 183901-63-5 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl trichloroacetimidate 
• 113567-42-3 5'-O-<<<<(2'',3'',4'',6''-tetra-O-benzoyl-α-D-mannopyranosyl)oxy>carbonyl>amino>sulfonyl>uridine 
• 1218904-60-9 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-N,N,N',N'-tetraisopropylphosphorodiamidite 
• 865470-38-8 3-butenyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranoside 
• 125367-09-1 n-pent-4-enyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranoside 
• 128503-39-9 methyl 2,3,4-tri-O-benzoyl-6-O-(2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl)-α-D-glucopyranoside 
• 118579-76-3 methyl 4-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-2,3,6-tri-O-benzyl-α-D-glucopyranoside 
• 149707-76-6 O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl) trichloroacetimidate 
• 149707-75-5 2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl trichloroacetimidate 

Relevant academic research and scientific papers

GLUCOSE-RESPONSIVE INSULIN CONJUGATES

Glucose-responsive insulin conjugates that contain one or more trisaccharides are provided. Such insulin conjugates may display a pharmacokinetic (PK) and/or pharmacodynamic (PD) profile that is responsive to the systemic concentrations of a saccharide such as glucose or alpha-methylmannose, even when administered to a subject in need thereof in the absence of an exogenous multivalent saccharide-binding molecule.

Carbon tetrachloride-free allylic halogenation-mediated glycosylations of allyl glycosides

The allylic bromination of allyl glycosides is conducted using NBS/AIBN reagents in (EtO)2CO and PhCF3 solutions, without using CCl4 as a solvent. The activated mixed halo-allyl glycosides led to glycosylations, mediated by a triflate, in a latent-active

Lewis acid promoted anomerisation of alkyl O- and S-xylo-, arabino- and fucopyranosides

Pentopyranoside and 6-deoxyhexopyranosides, such as those from D-xylose, L-arabinose and L-fucose are components of natural products, oligosaccharides or polysaccharides. Lewis acid promoted anomerisation of some of their alkyl O- and S-glycopyranosides i

Glycosylation with 3,5-Dimethyl-4-(2′-phenylethynylphenyl)phenyl (EPP) Glycosides via a Dearomative Activation Mechanism

A highly effective and versatile glycosylation method is developed, which uses 3,5-dimethyl-4-(2′-phenylethynylphenyl)phenyl (EPP) glycosides as donors and NIS/TMSOTf as promoter and proceeds via an unprecedented dearomative activation mechanism.

2′-Deoxy-2′,2′-difluorothymidine analogues for radiolabeling with fluorine-18 and other biomedical applications

Novel 2′-deoxy-2′,2′-difluorothymidine analogues with potential applications as antiviral, cytotoxic and cancer imaging agents have been synthesized. Introduction of the hydroxymethyl functionality at the 5-position of 2′-deoxy-2′,2′-difluoruridine provided a key intermediate with a suitable synthetic handle for the generation of these nucleoside derivatives.

Synthesis of a 1,3 β-glucan hexasaccharide designed to target vaccines to the dendritic cell receptor, Dectin-1

Transformation of 3-O-benzyl-1,2:5,6-di-O-isopropylidene-α-d-glucofuranose into 2,4,6-tri-O-benzoyl-3-O-benzyl glucopyranosyl imidate proceeded efficiently via crystalline benzyl and per-benzoylated derivatives. This imidate glycosylated di-O-isopropylidene-α-d-glucofuranose in high yield and glycosylation of the disaccharide after removal of the 3′-O-benzyl ether afforded the β1,3 linked trisaccharide in excellent yield. Di- and trisaccharides imidates were readily prepared from the furanose terminated glycosylation products but both were unreactive in glycosylation reaction with the debenzylated di- and trisaccharide alcohols. The 3′-O-benzyl perbenzoylated disaccharide pyranose derivative could be selectively debenzoylated and converted to the corresponding perbenzoylated 4,6:4′,6′-di-O-benzylidene derivative. Lewis acid catalyzed glycosidation gave the selectively protected disaccharide ethylthioglycoside in good overall yield. Glycosidation of this thioglycoside donor with 5-methoxycarbonylpentanol gave the disaccharide tether glycoside and after catalytic removal of benzyl ether the resulting disaccharide alcohol was glycosylated by the thioglycoside in a 2+2 reaction to yield a tetrasaccharide. Repetition of selective deprotection of the terminal 3-O-benzyl ether followed by glycosylation by the disaccharide thioglycoside gave a protected hexasaccharide. Hydrogenolysis of this hexasaccharide followed by transesterification and second hydrogenolysis to remove a residual benzyl group gave the target hexasaccharide glycoside 1 as a Dectin-1 ligand functionalized to permit covalent attachment to glycoconjugate vaccines and thereby facilitate improved antigen processing by dendritic cells.

3-(Dimethylamino)-1-propylamine: A cheap and versatile reagent for removal of byproducts in carbohydrate chemistry

Inexpensive 3-(dimethylamino)-1-propylamine (DMAPA) was found to be effective in anomeric deacylation reactions giving 1-O deprotected sugars in high yield as precursors for the formation of imidate glycosyl donors. DMAPA was also found to be useful for removing excess reagents such as benzoyl chloride, tosyl chloride, and 2,2,2-trifluoro-N-phenylacetimidoyl chloride. The deacylation reaction could be conducted in moist THF and did not require chromatographic purification since an acidic wash was sufficient to remove excess reagent and the formed byproduct.

Saccharide-modified nanodiamond conjugates for the efficient detection and removal of pathogenic bacteria

The detection and removal of bacteria, such as E. coli in aqueous environments by using safe and readily available means is of high importance. Here we report on the synthesis of nanodiamonds (ND) covalently modified with specific carbohydrates (glyco-ND) for the precipitation of type 1 fimbriated uropathogenic E. coli in solution by mechanically stable agglutination. The surface of the diamond nanoparticles was modified by using a Diels-Alder reaction followed by the covalent grafting of the respective glycosides. The resulting glyco-ND samples are fully dispersible in aqueous media and show a surface loading of typically 0.1 mmol g-1. To probe the adhesive properties of various ND samples we have developed a new sandwich assay employing layers of two bacterial strains in an array format. Agglutination experiments in solution were used to distinguish unspecific interactions of glyco-ND with bacteria from specific ones. Two types of precipitates in solution were observed and characterized in detail by light and electron microscopy. Only by specific interactions mechanically stable agglutinates were formed. Bacteria could be removed from water by filtration of these stable agglutinates through 10 μm pore-size filters and the ND conjugate could eventually be recovered by addition of the appropriate carbohydrate. The application of glycosylated ND allows versatile and facile detection of bacteria and their efficient removal by using an environmentally and biomedically benign material. Copyright

Cross metathesis assisted solid-phase synthesis of glycopeptoids

A solid-phase synthesis of glycopeptoids was explored through olefin cross metathesis (CM). Peptoids and sugar derivatives with appropriate olefin moieties were coupled in the presence of an olefin metathesis catalyst to afford glycopeptoids in good yield

1,2-Trans-selective synthesis of glycosyl boranophosphates and their utility as building blocks for the synthesis of phosphodiester-linked disaccharides

Figure Presented A highly 1,2-trans-selective synthesis of glycosyl boranophosphate derivatives by glycosylation of dimethyl boranophosphate with glycosyl iodides was developed. A study on the reaction mechanism indicated that the stereoselectivity of the