6341-06-6

Basic information

• Product Name: 1,2,3,4-Butanetetrol,1-(2-phenyl-2H-1,2,3-triazol-4-yl)-, (1R,2S,3R)-
• Synonyms: 1,2,3,4-Butanetetrol,1-(2-phenyl-2H-1,2,3-triazol-4-yl)-, D-arabino- (8CI); 1,2,3,4-Butanetetrol,1-(2-phenyl-2H-1,2,3-triazol-4-yl)-, [1R-(1R*,2S*,3R*)]-; 2H-1,2,3-Triazole,1,2,3,4-butanetetrol deriv.; D-Glucose, phenylosotriazole; Glucosephenylosotriazole
• CAS NO: 6341-06-6
• Molecular Formula: C12H15 N3 O4
• Molecular Weight: 265.269
• Mol File: 6341-06-6.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 1,2,3,4-Butanetetrol,1-(2-phenyl-2H-1,2,3-triazol-4-yl)-, (1R,2S,3R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3,4-Butanetetrol,1-(2-phenyl-2H-1,2,3-triazol-4-yl)-, (1R,2S,3R)-(6341-06-6)
• EPA Substance Registry System: 1,2,3,4-Butanetetrol,1-(2-phenyl-2H-1,2,3-triazol-4-yl)-, (1R,2S,3R)-(6341-06-6)

Safety Data

• Hazardous Substances Data: 6341-06-6(Hazardous Substances Data)

Upstream product

• 6032-23-1 L-arabino-[2]hexosulose bis-phenylhydrazone 
• 5440-70-0 L-(1S)-1-(2-phenyl-2H-[1,2,3]triazol-4-yl)-erythritol 
• 46994-10-9 4-(D-xylo-tetritol-1-yl)-2-phenyl-2H-1,2,3-triazole 
• 15476-34-3 L_r-1cat_F-1-(2-phenyl-2H-[1,2,3]triazol-4-yl)-butane-1c_F,2t_F,3r_F,4-tetraol 
• 50-99-7 D-glucose 
• 2280-44-6 D-Glucose 
• 100-63-0 phenylhydrazine 
• 67-56-1 methanol 
• 534-97-4 glucosazone 
• 7732-18-5 water 

Downstream Products

• 5440-70-0 DL-(1RS)-1-(2-phenyl-2H-[1,2,3]triazol-4-yl)-erythritol 
• 3213-80-7 2-phenyl-1,2,3-triazole-4-carboxaldehyde 
• 13306-99-5 2-phenyl-2H-[1,2,3]triazole-4-carboxylic acid 
• 188964-33-2 β-D-erythrofuranosyl-2-phenyl-2H-1,2,3-triazole 
• 18402-97-6 α-D-erythrofuranosyl-2-phenyl-2H-1,2,3-triazole 
• 6206-85-5 2-phenyl-1,2,3-triazole-4-formaldehyde oxime 
• 3359-24-8 2-(2-phenyl-2H-1,2,3-triazole-4-yl)methanol 
• 1578191-48-6 4-(ethoxymethyl)-2-phenyl-2H-1,2,3-triazole 
• 1578191-50-0 4-(butoxymethyl)-2-phenyl-2H-1,2,3-triazole 
• 1578191-46-4 (2-phenyl-2H-1,2,3-triazole-4-yl)methyl benzoate 
• 329695-11-6 (2-phenyl-2H-1,2,3-triazole-4-yl)methyl acetate 
• 1578191-44-2 (2-phenyl-2H-1,2,3-triazole-4-yl)methyl hexanoate 
• 1578191-43-1 (2-phenyl-2H-1,2,3-triazole-4-yl)methyl decanoate 
• 1339003-34-7 2-phenyl-4-vinyl-2H-1,2,3-triazole 

Relevant articles and documents

A fine-tuned lipophilicity/hydrophilicity ratio governs antibacterial potency and selectivity of bifurcated halogen bond-forming nbtis

Herein, we report the design of a focused library of novel bacterial topoisomerase inhibitors (NBTIs) based on innovative mainly monocyclic right-hand side fragments active against DNA gyrase and Topo IV. They exhibit a very potent and wide range of antibacterial activity, even against some of the most concerning hard-to-treat pathogens for which new antibacterials are urgently needed, as reported by the WHO and CDC. NBTIs enzyme activity and whole cell potency seems to depend on the fine-tuned lipophilicity/hydrophilicity ratio that governs the permeability of those compounds through the bacterial membranes. Lipophilicity of NBTIs is apparently optimal for passing through the membrane of Gram-positive bacteria, but the higher, although not excessive lipophilicity and suitable hydrophilicity seems to determine the passage through Gram-negative bacterial membranes. However, due to the considerable hERG inhibition, which is still at least two orders of magnitude away from MICs, continued optimization is required to realize their full potential.

Highly efficient and selective biocatalytic acylation studies on triazolylsugars

Different acid anhydrides (of C2 to C7 aliphatic fatty acids and benzoic acid) have been used to study the selective acylation of primary/secondary hydroxyl groups in 2-phenyl-4-(D-threo-1′,2′, 3′-trihydroxypropyl)-2H-1,2,3-triazole, 2-phenyl-4-(D-erythro-1′, 2′,3′-trihydroxypropyl)-2H-1,2,3-triazole, 2-phenyl-4-(D-arabino- 1′,2′,3′,4′-tetrahydroxybutyl)-2H-1,2,3-triazole and 2-phenyl-4-(D-lyxo-1′,2′,3′,4′-tetrahydroxybutyl)-2H-1, 2,3-triazole in the presence of Candida antarctica lipase B in diisopropyl ether. Among the different acid anhydrides, butanoic anhydride was found to be the most efficient acylating agent (for butanoylation); for acetylation, vinyl acetate gave the best results. The reactions with both these acylating agents were highly selective and efficient yielding exclusively the monoacylated products in 95-99% yields in 1-5 h.

Synthesis and antiviral activity evaluation of novel 2-phenyl-4-(D-arabino-4′-cycloaminobutyl)triazoles: Acyclonucleosides containing unnatural bases

Five 2-phenyl-4-(D-arabino-4′-cycloamino-3′-hydroxy-O-1′,2′-isopropylidenebutyl)-2H-1,2,3-triazoles, acyclonucleosides containing unnatural bases have been synthesised by opening of the epoxide ring of 2-phenyl-4-(D-arabino-3′,4′-epoxy-O-1′,2′-isopropylidenebutyl)-2H-1,2,3-triazole with the corresponding cyclic amine in 70-85% yields. The starting arabino-epoxytriazole was prepared in five steps starting from D-glucose in an overall yield of 15%. All the five triazolylacycllonucleosides were unambiguously identified on the basis of their spectral data. The structure of one of the intermediates, that is 2-phenyl-4-(D-arabino-1′,2′,3′,4′-tetrahydroxybutyl)-2H-1,2,3-triazole was confirmed by its X-ray crystallographic studies. These acyclonucleosides were subjected to antiviral evaluation in CEM-SS cell-based anti HIV assay with the lymphocytropic virus strains HIV-1IIIB and HIV-1RF. Copyright