4064-06-6

Basic information

• Product Name: 1,2:3,4-Di-O-isopropylidene-D-galactopyranose
• Synonyms: DIACETONE-D-GALACTOSE;DIACETONE-ALPHA-D-GAL;1,2:3,4-DIISOPROPYLIDEN-ALPHA-D-GALACTOPYRANOSE;1,2,3,4-DI-O-ISOPROPYLIDENE-D-GALACTOPYRANOSE;1,2:3,4-DI-O-ISOPROPYLIDENE-D-GALACTOPYRANOSE;1,2:3,4-DI-O-ISOPROPYLIDENE-A-D-GALACTOPYRANOSE;1,2,3,4-DI-O-ISOPROPYLIDENE-ALPHA-D-GALACTOPYRANOSE;1,2:3,4-DI-O-ISOPROPYLIDENE-ALPHA-D-GALACTOPYRANOSE
• CAS NO: 4064-06-6
• Molecular Formula: C₁₂H₂₀O₆
• Molecular Weight: 260.28
• EINECS: 223-771-7
• Product Categories: Sugars, Carbohydrates & Glucosides;13C & 2H Sugars;Biochemistry;Galactose;O-Substituted Sugars;Sugars;Carbohydrates & Derivatives;carbohydrate
• Mol File: 4064-06-6.mol

Chemical Properties

• Melting Point: 120-122 °C
• Boiling Point: 117 °C0.015 mm Hg(lit.)
• Flash Point: 159.3 °C
• Appearance: Clear pale yellow to yellow/Viscous Paste
• Density: 1.143 g/mL at 25 °C(lit.)
• Vapor Pressure: 7.17E-07mmHg at 25°C
• Refractive Index: n20/D 1.466(lit.)
• Storage Temp.: 2-8°C
• Solubility: Soluble in Acetone, Chloroform and Methanol.
• PKA: 14.00±0.10(Predicted)
• BRN: 1345410
• CAS DataBase Reference: 1,2:3,4-Di-O-isopropylidene-D-galactopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2:3,4-Di-O-isopropylidene-D-galactopyranose(4064-06-6)
• EPA Substance Registry System: 1,2:3,4-Di-O-isopropylidene-D-galactopyranose(4064-06-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36/37-26
• WGK Germany: 3
• F: 3-9-21
• Hazardous Substances Data: 4064-06-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1,2:3,4-Di-O-isopropylidene-D-galactopyranose is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique structure allows for the development of new drugs with potential applications in treating various diseases.
Used in Biochemical Research:
In the field of biochemical research, 1,2:3,4-Di-O-isopropylidene-D-galactopyranose serves as a valuable tool for studying the structure and function of carbohydrates and their interactions with other biomolecules. Its protected hydroxyl groups facilitate the investigation of carbohydrate recognition and binding processes.
Used in Synthesis of Biochemical Compounds:
1,2:3,4-Di-O-isopropylidene-D-galactopyranose is used as a starting material for the production of diacetone-D-galacturonic acid and oxalic acid. These compounds have various applications in the biochemical industry, including the development of new drugs and the study of metabolic pathways.

InChI:InChI=1/C12H20O6/c1-11(2)15-7-6(5-13)14-10-9(8(7)16-11)17-12(3,4)18-10/h6-10,13H,5H2,1-4H3/t6-,7+,8+,9-,10-/m1/s1

Upstream product

• 18524-41-9 (3aR,5S,5aR,8aS,8bR)-methyl-2,2,7,7-tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4',5'-d]pyran-5-carboxylate 
• 4026-28-2 1,2:3,4-di-O-isopropylidene-6-iodo-D-galactopyranose 
• 35526-05-7 6-O-benzyl-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 
• 81712-60-9 (3aR,5R,5aS,8aS,8bR)-5-Benzhydryloxymethyl-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran 
• 67-64-1 acetone 
• 3396-99-4 methyl α-D-galactopyranoside 
• 59-23-4 D-Galactose 
• 59401-67-1 1,2:3,4-Di-O-isopropyliden-6-O-pentaflyl-α-D-galaktopyranose 
• 50-00-0 formaldehyd 
• 4933-77-1 (3aR,5S,5aR,8aS,8bR)-2,2,7,7-Tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-carbaldehyde 
• 4148-55-4 (-)-1,2:3,4-di-O-isopropylidene-6-O-methylsulfonyl-α-D-galactopyranose 
• 294637-35-7 6-O-(4-(N-methyl-N-phenylamino)benzyl)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranoside 
• 294637-36-8 6-O-(4-(N-morpholino)benzyl)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranoside 
• 294637-37-9 6-O-(2-(N-benzylamino)benzyl)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranoside 

Downstream Products

• 4860-78-0 6-O-acetyl-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 
• 76951-66-1 1,2:3,4-di-O-isopropylidene-6-O-trityl-α-D-galactopyranose 
• 4478-43-7 (1,2:3,4-di-O-isopropylidene-6-O-(p-toluensulfonate))-D-galactopiranose 
• 119646-32-1 diphenyl (1,2:3,4-di-O-isopropylidene-α-D-galactopyranosyl)-6-O-phosphate 
• 60945-40-6 O¹,O²-isopropylidene-α-D-galactopyranose 
• 25253-46-7 (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 
• 99458-24-9 (2R,3S)-3-Benzoylamino-2-benzyloxymethoxy-3-phenyl-propionic acid (3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethyl ester 
• 131919-43-2 C₄₆H₄₆O₁₅ 
• 129492-27-9 1,2:3,4-bis-O-(1-methylethylidene)-6-O-(2-pyridinylmethyl)-α-D-galactopyranose 
• 1824-93-7 methyl-β-D-galactofuranoside 
• 3396-99-4 methyl α-D-galactopyranoside 
• 64842-82-6 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->6)-[1:2,3:4]-di-O-isopropylidene-α-D-galactopyranoside 
• 41671-29-8 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl-(1->6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranoside 
• 139378-96-4 6'-(1',2':3',4'-diisopropylidenegalactopyranosyl) 3-O-benzyl-2-deoxy-2-(phenylthio)-β-D-glucopyranoside 

Relevant articles and documents

Rapid synthesis of 1-deoxygalactonojirimycin using a carbamate annulation

A remarkably efficient synthesis of the biologically important iminosugar 1-deoxygalactonojirimycin (DGJ) is presented. Key to this strategy is the development of a novel carbamate annulation reaction that favours formation of a six-membered carbamate-containing piperidine skeleton over its five-membered counterpart.

Covalent Lectin Inhibition and Application in Bacterial Biofilm Imaging

Biofilm formation by pathogenic bacteria is a hallmark of chronic infections. In many cases, lectins play key roles in establishing biofilms. The pathogen Pseudomonas aeruginosa often exhibiting various drug resistances employs its lectins LecA and LecB as virulence factors and biofilm building blocks. Therefore, inhibition of the function of these proteins is thought to have potential in developing “pathoblockers” preventing biofilm formation and virulence. A covalent lectin inhibitor specific to a carbohydrate binding site is described for the first time. Its application in the LecA-specific in vitro imaging of biofilms formed by P. aeruginosa is also reported.

Hypervalent iodine system for debenzylation of sugars

A simple and mild system using 4,4′-bis-(dichloroiodo)-biphenyl in combination with tetraethylammonium bromide (TEAB) at room temperature has been developed for selective debenzylation of sugars. Acetates, benzoate, and sensitive glycosidic linkages are unaffected. Copyright Taylor & Francis Group, LLC.

Thermoresponsive copolymers with pendant d-galactosyl 1,2,3-triazole groups: Synthesis, characterization and thermal behavior

A galactose containing glycomonomer has been synthesized by copper catalyzed azide-alkyne cyclo-addition reaction (CuAAC) of 6-azido-6-deoxy-1,2:3,4-di-O-isopropylidene-α-d-galactopyranose with propargyl acrylate. This monomer was subjected to homopolymerization and copolymerization with N-isopropylacrylamide (NIPAm) at different compositions by free radical polymerization using 2,2′-azobis-isobutyronitrile (AIBN) as an initiator. The composition of the copolymer was determined by 1H-NMR spectroscopy. Upon acid hydrolysis of acetonide protected polymers, water-soluble deprotected polymers were obtained. The polymers were characterized and confirmed by NMR, IR, GPC and thermal analytical techniques. The protected and deprotected copolymers showed a sharp cloud-point temperature and a linear correlation was obtained between the lower critical solution temperatures (LCST) and the concentration of glycomonomer in the copolymers. This allows tuning the thermal response by simply altering the copolymer composition. Water contact angle experiments showed the changes in the hydrophilicity of copolymers with compositions that supported the LCST results. The glass transition temperature of protected copolymers followed a regular monotonic decreasing trend with increasing glycomonomer content, whereas Tg of deprotected copolymers increased due to H-bond interaction. The attempts to develop thermoresponsive polymers having LCSTs at physiological temperature were successful.

Synthesis of new five membered nitrogen containing heterocycles bearing D-galactose side chains

The synthesis of 5-[6'-deoxy-(1',2':3',4'-di-O-isopropylidene-α-D-galactopyranos-6'-yl)]tetra zole and its reaction with acetic anhydride and 1,2:3,4-di-O-isopropylidene-6-O-(4-toluenesulfonyl)-α-D-galactopyranose are described.

Synthesis of amphiphilic galactopyranosyl diamines and amino alcohols as antitubercular agents

Mono- and diacylated derivatives of galactopyranosyl amines were obtained from d-galactose, via aminated intermediates prepared by reaction of 6-deoxy-6-iodo-1,2:3,4-di-O-isopropylidene-α-d-galactopyranose with 1,3-propanediamine, 1,2-ethanediamine or ethanolamine. Monoacylated derivatives displayed antitubercular activity.

Synthesis, spectroscopic studies, and x-ray crystallographic analysis of the organotin carbohydrate: 1,2:3,4-di-O-isopropylidene-6-O-triphenylstannylmethyl-α-D-galactopyranose

The title organotin carbohydrate, C31H36O6Sn, has been synthesized and its molecular structure has been determined in solution and in the solid state.NMR, infrared, mass and X-ray crystallographic techniques were used.The chiral molecules crystallize in the monoclinic space group P21 with Z=2.The triphenyltin and carbohydrate moieties are linked by a trans methylene-oxygen-methylene arrangement.The pyranosyl ring adopts a twist-boat conformation and the isopropylidene rings adopt different (half-chair and envelope) forms.Solution and solid-state conformations are similar as only three Δ 13C shift values are greater than 2ppm; the Δ 119Sn value is 12 ppm.KEY WORDS: X-ray crystallographic analysis; organotin; carbohydrate.

Helical Self-Assembly of Optically Active Glycoconjugated Phthalocyanine J-Aggregates

Four galactoconjugated zinc(II) phthalocyanines (Pcs) have been prepared and fully characterized. The carbohydrate-containing phthalonitrile precursors of the Pcs were synthesized through a copper-catalysed azide-alkyne cycloaddition (CuAAC). The Pcs show a remarkable aggregation behaviour in solution, depending on the nature of the solvent, the temperature and the substitution position on the phthalocyanine. Solvent-dependent CD-spectroscopy experiments show that these Pcs aggregate as chiral helices in solution. Crystal structure data of a phthalocyanine bearing two carbohydrate units substantiate the properties shown by CD spectroscopy. Furthermore, the 1,2,3-triazole moieties of the Pcs play a decisive role in the formation of supramolecular aggregates. The glycoconjugated zinc(II) phthalocyanines described here show molar extinction coefficients ?max>105 M?1 cm?1 and absorption maxima λmax>680 nm, which make them attractive photosensitizers for Photodynamic Therapy (PDT).

Conformation of the Galactose Ring Adopted in Solution and in Crystalline Form as Determined by Experimental and DFT 1H NMR and Single-Crystal X-ray Analysis

The solution-state conformations of various galactose derivatives were determined by comparison of the experimental 1H-1H vicinal coupling constants to those calculated using density functional theory (DFT) at the B3LYP/cc-pVTZ//B3LYP/6-31G(d,p) level of theory. The agreement between the experimental and calculated vicinal coupling constants for 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose was good, thereby confirming an OS2 skew conformation for it and its derivatives on the basis of their similar observed couplings. Single-crystal X-ray analysis of 1,2:3,4-di-O-isopropylidene-6-O-(3,4, 6-tri-O-acetyl-2-deoxy-2-N-phthalimido-β-D-glucopyranosyl) -α-D-galactopyranose and 1,2,3,4,6-penta-O-acetyl-α -D-galactopyranose provided OS2 and 4C 1 conformations, respectively, for the galactose ring in the solid state. The solid-state structures proved to be suitable starting structures for further DFT structure refinement or for immediate calculation of the coupling constants.

Epoc group: Transformable protecting group with gold(iii)-catalyzed fluorene formation

This study presents the novel concept of a transformable protecting group, which changes its properties through structural transformation. Based on this concept, we developed a 2-(2-ethynylphenyl)-2-(5-methylfuran-2-yl)-ethoxycarbonyl (Epoc) group. The Epoc group was transformed into an Fmoc-like structure with gold(iii)-catalyzed fluorene formation and was removable under Fmoc-like mild basic conditions post-transformation even though it was originally stable under strongly basic conditions. As an application for organic synthesis, the Epoc group provides the novel orthogonality of gold(iii)-labile protecting groups in solid-phase peptide synthesis. In addition, the high turnover number of fluorene formation in aqueous media is suggestive of the applicability of the Epoc group to biological systems. This journal is