139888-80-5

Basic information

• Product Name: 2-azidoethyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside
• Synonyms: 2-azidoethyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside
• CAS NO: 139888-80-5
• Molecular Weight: 417.373
• Mol File: 139888-80-5.mol
• Article Data: 42

Chemical Properties

• CAS DataBase Reference: 2-azidoethyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: 2-azidoethyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside(139888-80-5)
• EPA Substance Registry System: 2-azidoethyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside(139888-80-5)

Safety Data

• Hazardous Substances Data: 139888-80-5(Hazardous Substances Data)

Upstream product

• 7296-64-2 β-D-galactopyranoside 
• 1517-05-1 2-azidoethanol 
• 25878-60-8 D-galactose pentaacetate 
• 74808-10-9 2,3,4,6-tetra-O-acetyl-D-galactopyranosyl trichloroacetimidate 
• 3947-62-4 2,3,4,6-tetra-O-acetyl-α/β-D-galactopyranose 
• 10257-28-0 D-Galactose 
• 540-51-2 2-bromoethanol 
• 4163-60-4 β-D-galactose peracetate 
• 70191-05-8 2,3,4,6-tetra-O-acetyl-β-D-galactopyranose 
• 16977-78-9 2-bromoethyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside 
• 108-24-7 acetic anhydride 
• 86520-63-0 2,3,4,6-tetra-O-acetyl-α-galactopyranosyl trichloroacetimidate 
• 16977-77-8 2-chloroethyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside 
• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 

Relevant articles and documents

Site-selective modification of proteins for the synthesis of structurally defined multivalent scaffolds

A combination of classical site-directed mutagenesis, genetic code engineering and bioorthogonal reactions delivered a chemically modified barstar protein with one or four carbohydrates installed at specific residues. These protein conjugates were employed in multivalent binding studies, which support the use of proteins as structurally defined scaffolds for the presentation of multivalent ligands.

Neutral Re(I) Complex Platform for Live Intracellular Imaging

Luminescent metal complexes are a valuable platform for the generation of cell imaging agents. However, many metal complexes are cationic, a factor that can dominate the intracellular accumulation to specific organelles. Neutral Re(I) complexes offer a more attractive platform for the development of bioconjugated imaging agents, where charge cannot influence their intracellular distribution. Herein, we report the synthesis of a neutral complex (ReAlkyne), which was used as a platform for the generation of four carbohydrate-conjugated imaging agents via Cu(I)-catalyzed azide-alkyne cycloaddition. A comprehensive evaluation of the physical and optical properties of each complex is provided, together with a determination of their utility as live cell imaging agents in H9c2 cardiomyoblasts. Unlike their cationic counterparts, many of which localize within mitochondria, these neutral complexes have localized within the endosomal/lysosomal network, a result consistent with examples of dinuclear carbohydrate-appended neutral Re(I) complexes that have been reported. This further demonstrates the utility of these neutral Re(I) complex imaging platforms as viable imaging platforms for the development of bioconjugated cell imaging agents.

Neoglycopeptides through direct functionalization of cysteine

Neoglycopeptides are readily prepared by direct functionalization of cysteine-containing peptides followed by click triazole formation between the resulting propargylated peptides and protected or free (2-azido)-ethyl gluco-, manno,- and galactopyranosides.

Lectin recognition of a new SOD mimic bioconjugate studied with surface plasmon resonance imaging

Surface plasmon resonance imaging is used to demonstrate the recognition by the Ricinus communis agglutinin of a new SOD mimic, a bioconjugate of the manganese(ii) complex of 1,4,7,10,13-pentaazacyclopentadecane with galactose. The Royal Society of Chemistry.

Synthesis and Characterization of Novel Fluoro-glycosylated Porphyrins that can be Utilized as Theranostic Agents

Small molecules with modalities for a variety of imaging techniques as well as therapeutic activity are essential, as such molecules render opportunities to simultaneously conduct diagnosis and targeted therapy, so called theranostics. In this regard, gly

Sym-(CH2X)5-corannulenes: Molecular pentapods displaying functional group and bioconjugate appendages

Pentapodal ω-functional derivatives of corannulene have been synthesized from sym-pentachlorocorannulene by iron-catalyzed aryl-alkyl cross coupling reactions. Click chemistry gives access to pentapods with bioconjugate appendages.

On-Bead Peptoid Dimerization Induced by Incorporation of Glycosylated Bridging Units in Submonomer Solid-Phase Approach to Glycopeptoids

A study on submonomer solid-phase synthesis of S-glycopeptoids has been carried out by screening different parameters. Dimeric species, featuring glycosylated bridging amino monomers, were found under suitable conditions. These dimers arise from an on-res

Synthesis of carbohydrate-functionalized thiophene-capped cyclopenta[c]thiophene for concanavalin A recognition

Synthetic route to two different carbohydrate-functionalized oligothiophenes comprising central cyclopenta[c]thiophene (CPT) moiety was demonstrated. Turbidimetric analysis revealed enhanced interaction for divalent α-mannose-functionalized terthiophene 7 with Con A. The extent of binding interaction for 7-Con A complex formation was determined from isothermal titration calorimetry (ITC) measurements and the binding constant found (K ITC) 2.4(6) × 105 M-1.

Synthesis of New C-2 Triazole-Linked Analogs of Triterpenoid Pentacyclic Saponins

C-2 mono- and bis-1,2,3-triazole-linked analogs of lupane, ursane, and oleane triterpenoid saponins were synthesized for the first time using regioselective Cu(I)-catalyzed 1,3-dipolar cycloaddition (CuAAC) of peracetylated sugar azides and C-2 propynyl derivatives of triterpene acids. Cytotoxic activity of the synthesized compounds was studied in vitro at the National Cancer Institute (USA). Several of the synthesized compounds exhibited weak cytotoxic activity.

Visible-Light-Mediated Click Chemistry for Highly Regioselective Azide–Alkyne Cycloaddition by a Photoredox Electron-Transfer Strategy

Click chemistry focuses on the development of highly selective reactions using simple precursors for the exquisite synthesis of molecules. Undisputedly, the CuI-catalyzed azide–alkyne cycloaddition (CuAAC) is one of the most valuable examples of click chemistry, but it suffers from some limitations as it requires additional reducing agents and ligands as well as cytotoxic copper. Here, we demonstrate a novel strategy for the azide–alkyne cycloaddition reaction that involves a photoredox electron-transfer radical mechanism instead of the traditional metal-catalyzed coordination process. This newly developed photocatalyzed azide–alkyne cycloaddition reaction can be performed under mild conditions at room temperature in the presence of air and visible light and shows good functional group tolerance, excellent atom economy, high yields of up to 99 %, and absolute regioselectivity, affording a variety of 1,4-disubstituted 1,2,3-triazole derivatives, including bioactive molecules and pharmaceuticals. The use of a recyclable photocatalyst, solar energy, and water as solvent makes this photocatalytic system sustainable and environmentally friendly. Moreover, the azide–alkyne cycloaddition reaction could be photocatalyzed in the presence of a metal-free catalyst with excellent regioselectivity, which represents an important development for click chemistry and should find versatile applications in organic synthesis, chemical biology, and materials science.