25253-46-7

Basic information

• Product Name: 1,2,3,4-DI-O-ISOPROPYLIDENE-ALPHA-D-GALACTURONIC ACID
• Synonyms: 1,2:3,4-DI-O-ISOPROPYLIDENE-ALPHA-D-GALACTOPYRANURONIC ACID;1,2,3,4-DI-O-ISOPROPYLIDENE-ALPHA-D-GALACTURONIC ACID;1,2:3,4-Di-O-isopropylidene-a-D-galacturonide;1,2:3,4-Di-O-isopropylidene-α-D-galactopyranuronic acid;1-O,2-O:3-O,4-O-Diisopropylidene-6-oxo-α-D-galactopyranose;1-O,2-O:3-O,4-O-Diisopropylidene-α-D-galactopyranuronic acid;1,2:3,4-di-O-isopropylidene-α-D-galactopyranosiduronic acid
• CAS NO: 25253-46-7
• Molecular Formula: C₁₂H₁₈O₇
• Molecular Weight: 274.27
• Mol File: 25253-46-7.mol
• Article Data: 26

Chemical Properties

• Melting Point: 152-153 °C
• Boiling Point: 386.5±42.0 °C(Predicted)
• Appearance: /
• Density: 1.251±0.06 g/cm3(Predicted)
• PKA: 2.62±0.60(Predicted)
• CAS DataBase Reference: 1,2,3,4-DI-O-ISOPROPYLIDENE-ALPHA-D-GALACTURONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3,4-DI-O-ISOPROPYLIDENE-ALPHA-D-GALACTURONIC ACID(25253-46-7)
• EPA Substance Registry System: 1,2,3,4-DI-O-ISOPROPYLIDENE-ALPHA-D-GALACTURONIC ACID(25253-46-7)

Safety Data

• Hazardous Substances Data: 25253-46-7(Hazardous Substances Data)

Usage

General Description

1,2,3,4-Di-O-isopropylidene-alpha-D-galacturonic acid is a chemical compound primarily used in the synthesis of various organic compounds and pharmaceutical intermediates. It is a derivative of galacturonic acid, a sugar acid derived from the oxidation of galactose. The di-isopropylidene group in the compound serves to protect the aldehyde group in the galacturonic acid, making it useful in organic synthesis reactions. 1,2,3,4-DI-O-ISOPROPYLIDENE-ALPHA-D-GALACTURONIC ACID is commonly used in the production of glycosidic compounds and can also be utilized in the preparation of heterocyclic compounds. Additionally, 1,2,3,4-Di-O-isopropylidene-alpha-D-galacturonic acid has potential applications in the pharmaceutical industry, particularly in the development of new drugs and therapeutic agents.

Upstream product

• 4064-06-6 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 
• 10257-28-0 D-Galactose 
• 110319-61-4 1,2:3,4-di-O-isopropylidene-β-D-galactopyranose 
• 3646-73-9 α-D-galactopyranose 
• 59-23-4 D-Galactose 
• 118893-76-8 C₂₆H₂₄O₈ 
• 118920-26-6 C₂₃H₂₀O₈ 
• 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 
• 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 
• 685-73-4 D-galacturonic acid 

Downstream Products

• 4064-06-6 1,2:3,4-di-O-isopropylidene-α-L-galactopyranose 
• 4064-06-6 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 
• 104109-87-7 (1,2:3,4-di-O-isopropylidene-α-D-galactopyranuronyl)-(triphenylphosphoranylidene)methane 
• 1151539-61-5 C₂₃H₃₂N₂O₉ 
• 1151539-59-1 (1,2)(3,4)-diacetylgalactopyranosyl-6-NH-CO-NH-Phe-OMe 
• 129439-75-4 Benzyl(1,2,3,4-tetra-O-acetyl-α-D-galactopyranose)uronat 
• 129439-75-4 benzyl (1,2,3,4-tetra-O-acetyl-α/β-D-galactopyranose)uronate 
• 122128-13-6 (3aR,5S,5aR,8aS,8bR)-2,2,7,7-Tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-carboxylic acid (2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester 
• 122128-13-6 (3aR,5S,5aR,8aS,8bR)-2,2,7,7-Tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-carboxylic acid (2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester 

Relevant articles and documents

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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.

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