25253-46-7

Usage

Uses

Used in Organic Synthesis:
1,2,3,4-Di-O-isopropylidene-alpha-D-galacturonic acid is used as a key intermediate in the synthesis of organic compounds for various applications, including the production of glycosidic compounds and heterocyclic compounds. Its protective di-isopropylidene group facilitates controlled reactions in organic synthesis processes.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 1,2,3,4-Di-O-isopropylidene-alpha-D-galacturonic acid is utilized as a pharmaceutical intermediate for the development of new drugs and therapeutic agents. Its unique structure and reactivity make it a valuable component in the creation of innovative medicinal compounds.
Used in the Synthesis of Glycosidic Compounds:
1,2,3,4-Di-O-isopropylidene-alpha-D-galacturonic acid is used as a building block in the synthesis of glycosidic compounds, which are essential in various biological processes and have potential applications in drug discovery and development.
Used in the Preparation of Heterocyclic Compounds:
1,2,3,4-DI-O-ISOPROPYLIDENE-ALPHA-D-GALACTURONIC ACID is also used in the preparation of heterocyclic compounds, which are important in the field of medicinal chemistry and can be found in a wide range of pharmaceuticals and agrochemicals. The versatility of 1,2,3,4-Di-O-isopropylidene-alpha-D-galacturonic acid allows for the creation of diverse heterocyclic structures with potential therapeutic properties.

Upstream product

• 4064-06-6 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 
• 118893-77-9 (3aR,5S,6R,7S,7aR)-5-Furan-2-yl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6,7-diol 
• 118893-76-8 C₂₆H₂₄O₈ 
• 118920-26-6 C₂₃H₂₀O₈ 
• 99166-39-9 (3aR,5S,5aR,8aS,8bR)-5-Furan-2-yl-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran 
• 59-23-4 D-Galactose 
• 3646-73-9 α-D-galactopyranose 
• 110319-61-4 1,2:3,4-di-O-isopropylidene-β-D-galactopyranose 
• 10257-28-0 D-Galactose 
• 685-73-4 D-galacturonic acid 

Downstream Products

• 99166-47-9 Benzoic acid (2R,3S,4R)-2-[(R)-benzyloxy-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-methyl]-4-hydroxy-3,4-dihydro-2H-pyran-3-yl ester 
• 99166-46-8 (2R,3R)-2-(6-O-benzyl-1,2,3,4-di-O-isopropylidene-D-glycero-α-D-galacto-1,5-pyranosyl)-3-benzyloxy-2,3-dihydro-4H-pyran-4-one 
• 118893-79-1 6-O-benzyl-1,2,3,4-di-O-isopropylidene-D-glycero-D-galacto-D-galacto-undecapyranose 
• 99166-48-0 (3S,4S,5S,6S)-6-[(R)-Benzyloxy-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-methyl]-tetrahydro-pyran-2,3,4,5-tetraol 
• 119007-08-8 Acetic acid (E)-(R)-3-benzyloxy-3-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-propenyl ester 
• 99212-55-2 6,7,8,9,10,11-hexa-O-benzyl-1,2,3,4-di-O-isopropylidene-D-glycero-D-galacto-D-galacto-undecapyranose 
• 91861-00-6 6-O-benzyl-1,2:3,4-di-O-isopropylidene-α-D-glycero-D-galacto-heptodialdo-1,5-pyranose 
• 99166-44-6 (R)-3-Benzyloxy-3-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-propionaldehyde 
• 99166-43-5 (3aR,5R,5aS,8aS,8bR)-5-((R)-1-Benzyloxy-but-3-enyl)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran 

Relevant academic research and scientific papers

Transition-Metal-Free Synthesis of C-Glycosylated Phenanthridines via K2S2O8-Mediated Oxidative Radical Decarboxylation of Uronic Acids

We have developed an efficient protocol for the synthesis of C-glycosylated phenanthridines. Tetrafuranos-4-yl and pentapyranos-5-yl radicals, generated from K2S2O8-mediated oxidative decarboxylation of furan- and pyranuronic acids, undergo attack to 2-isocyanodiphenyls and ensuing homolytic aromatic substitution to provide diverse C-glycosylated phenanthridines in satisfactory yields without resort to transition metals. This reaction tolerates various functional groups, and enables ready synthesis of complex oligosaccharide-based phenanthridines. The C-glycosylated phenanthridine derived from β-cyclodextrin has been prepared, which might be potential in medicinal and biological chemistry due to its flexible conformation.

Synthesis of three different galactose-based methacrylate monomers for the production of sugar-based polymers

Glycopolymers, synthetic sugar-containing macromolecules, are attracting ever-increasing interest from the chemistry community. Glycidyl methacrylate (GMA) is an important building block for the synthesis of sugar based methacrylate monomers and polymers. Normally, glycidyl methacrylate shows some advantages such as reactivity against nucleophiles or milder synthetic conditions such as other reactive methacrylate monomers. However, condensation reactions of glycidyl methacrylate with for instance protected galactose monomer leads to a mixture of two products due to a strong competition between the two possible pathways: epoxide ring opening or transesterification. In this paper, we propose two alternative routes to synthesize regiospecific galactose-based methacrylate monomers using the epoxy-ring opening reaction. In the first alternative route, the protected galactose is first oxidized to the acid in order to make it more reactive against the epoxide of GMA. In the second route, the protected sugar was first treated with epichlorohydrin followed by the epoxy ring opening reaction with methacrylic acid, to create an identical analogue of the ring-opening product of GMA. These two monomers were polymerized using conventional radical polymerization and were compared to the previously known galactose-methacrylate one. The new polymers show similar thermal stability but lower glass transition temperature (Tg) with respect to the known galactose methacrylate polymer.

Glyco- and peptidomimetics from three-component joullie-ugi coupling show selective antiviral activity

Chlorination-elimination chemistry coupled with three-component Joullie-Ugi reaction and facile deprotection allowed efficient access to an array of polyhydroxylated pyrrolidines through parallel synthesis that may be considered to be a library of imino (

Visible-Light-Mediated, Chemo- and Stereoselective Radical Process for the Synthesis of C-Glycoamino Acids

An approach for efficient synthesis of C-glycosyl amino acids is described. Different from typical photoredox-catalyzed reactions of imines, the new process follows a pathway in which α-imino esters serve as electrophiles in chemoselective addition reactions with nucleophilic glycosyl radicals. The process is highlighted by the mild nature of the reaction conditions, the highly stereoselectivity attending C-C bond formation, and its applicability to C-glycosylations using both armed and disarmed pentose and hexose derivatives.

A highly efficient TEMPO mediated oxidation of sugar primary alcohols into uronic acids using 1-chloro-1,2-benziodoxol-3(1H)-one at room temperature

Oxidation of various sugar primary alcohols into corresponding uronic acids was demonstrated using 1-chloro-1,2-benziodoxol-3(1H)-one and TEMPO. The reaction proceeds at room temperature in good to excellent yields. Primary alcohols get oxidized selective

I2/PPh3-mediated facile synthesis of glycoconjugated N-acylbenzotriazoles

A well-stabilized method for synthesis of N-acylbenzotriazoles from carboxylic acids using I2/PPh3 in anhydrous dichloromethane has been extended in glycochemistry to synthesize glycoconjugated N-acylbenzotriazoles with high yields at room temperature in 2-hour reaction time.

A green and sustainable phosphine-free NHC-ruthenium catalyst for selective oxidation of alcohols to carboxylic acids in water

In this work, we present a new catalytic system for the selective dehydrogenative oxidation of primary alcohols to carboxylic acids using a phosphine-free NHC-ruthenium catalyst in water under mild reaction conditions. With this catalytic system, a variety of primary alcohols have been converted to carboxylic acids respectively, in aqueous media, without using any additional oxidant; the only side product in this reaction is molecular hydrogen. This novel synthetic protocol is applied for direct oxidation of biologically active monosaccharides and polymers with primary alcohol groups in the side chain. The use of water as a solvent and oxygen donor as well as the absence of any toxic oxidizing agent make this atom economical reaction interesting from an environmental point of view.

Synthesis of novel glycopeptidomimetics via Nβ-protected- amino alkyl isonitrile based Ugi 4C reaction

The Ugi-4C reaction employing Nβ-protected-amino alkyl isonitrile, amino acid ester, aldehyde, and glycosyl acid has resulted in novel glycosylated peptidomimetics. The extension of MCR products for the synthesis of N,N′-orthogonally protected

TPAP-catalyzed direct oxidation of primary alcohols to carboxylic acids through stabilized aldehyde hydrates

We present a simple, mild, and highly effective method for the direct conversion of primary alcohols to carboxylic acids. TPAP serves as the catalyst, and NMO?H2O plays a dual role, acting as the co-oxidant and as a reagent for aldehyde hydrate stabilization. This previously unknown stabilizing effect of geminal diols by N-oxides is the key for the efficiency of the overall transformation.

Chiral lanthanoid dimers ligated by carbohydrate-based diketonates: Catalytic and luminescent properties

The reaction of hydrated lanthanoid chlorides (Ln = La, Eu) with chiral, carbohydrate-based diketonate ligands has yielded dimeric species with Ln 2L6 composition as determined by MALDI mass spectrometry and single-crystal X-ray crystallography. The X-ray crystallographic analysis identified a chiral cavity formed by interligand repulsion able to coordinate dimethylformamide, prompting investigation of the catalytic properties of the dimers. Preliminary results indicate that the dimers display catalytic activity in thio-Michael addition reactions as well as metal-based luminescence in the case of europium.