1075-59-8

Usage

Uses

4,?6-?dimethoxy-1,?3,?5-?Triazin-?2(1H)?-?one is a cyanuric acid (C987715) derivative and its cationic form is used as a leaving group for the rapid formation of carbocation species in the acid-?catalyzed alkylation of O- and C-?nucleophiles.

InChI:InChI=1/C5H7N3O3/c1-10-4-6-3(9)7-5(8-4)11-2/h1-2H3,(H,6,7,8,9)

Upstream product

• 5759-58-0 2,4,6-tris(methylthio)-1,3,5-triazine 
• 877-89-4 2,4,6-trimethoxy-1,3,5-triazine 
• 87024-55-3 N-(4,6-dimethoxy-1,3,5-triazin-2-yl)-N,N,N-trimethylammonium chloride 
• 1493-13-6 trifluorormethanesulfonic acid 
• 122-97-4 3-Phenyl-1-propanol 
• 42030-76-2 4-((4,6-dimethoxy-1,3,5-triazin-2-yl)oxy)benzaldehyde 
• 28690-95-1 2-(4-nitrophenoxy)-4,6-dimethoxy-1,3,5-triazine 
• 1237742-73-2 C₅₆H₉₁N₃O₄₅ 
• 1237742-72-1 C₄₄H₇₁N₃O₃₅ 
• 132353-25-4 2-(4-methoxybenzoyloxy)-4,6-dimethoxy-1,3,5-triazine 
• 768-60-5 4-methoxyphenylacetylen 
• 536-74-3 phenylacetylene 
• 766-97-2 4-n-methylphenylacetylene 
• 40307-11-7 1-ethyl-4-ethynylbenzene 

Downstream Products

• 419533-86-1 benzyl 4,6-dimethoxy-1,3,5-triazinyl carbonate 
• 454653-24-8 2,4-dimethoxy-6-trifluoromethanesulfonyloxy-1,3,5-triazine 
• 3140-73-6 2-chloro-4,6-dimethoxy-1 ,3,5-triazine 

Relevant academic research and scientific papers

4,6-dimethoxy-1,3,5-triazin-2-yl-d-glycosaminides: Novel substrates for transglycosylation reaction catalyzed by exo-d-glucosaminidase from amycolatopsis orientalis

A novel sugar adduct, 4,6-dimethoxy-1,3,5-triazin-2-yl-d-glucosaminide (GlcN-DMT), has been prepared by the reaction of d-glucosamine (GlcN) and 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-morpholinium chloride (DMT-MM). The adduct was recognized by exo-d-glucosaminidase (GlcNase) from Amycolatopsis orientalis and transferred the GlcN moiety, giving rise to the corresponding glucosaminides. This chemo-enzymatic process was successfully applied to d-galactosamine (GalN). GalN-DMT prepared directly from GalN and DMT-MM behaved as an efficient glycosyl donor for transfer of the GalN moiety catalyzed by the same enzyme. The introduction of the 4,6-dimethoxy-1,3,5-triazin-2-yl leaving group to the anomeric center significantly enhanced transglycosylating ability, resulting in the efficient glycosidase-catalyzed synthesis of glycosaminides.

Reaction of Potassium Salts of N-(Thio)phosphorylthioamides with Chlorinated 1,3,5-Triazines

Potassium salts of N-(thio)phosphorylthioamides can substitute one, two, or three halogen atoms in chlorinated 1,3,5-triazine molecules to give the products of imidothiyl structure. At low temperature, products of incomplete substitution of halogen in the

Optimized triazine-mediated amidation for efficient and controlled functionalization of hyaluronic acid

Triazine-based coupling agents have the potential to replace carbodiimides in the functionalization of hyaluronic acid (HA) giving derivatives with high degrees of substitution (DS) under mild conditions with excellent efficiency. Kinetics of the triazine

Cooperation of the Neutral and the Cationic Leaving Group Pathways in Acid-Catalyzed O-Benzylation of TriBOT

The reaction profile of acid-catalyzed O-benzylation with 2,4,6-tris(benzyloxy)-1,3,5-triazine (TriBOT) was analyzed to study the reaction kinetics. The first-order kinetic constant for the formation of benzyl cation species from N-protonated TriBOT (neutral leaving group pathway) was estimated and compared with that of the model compound for TriBOT. Since rapid consumption of TriBOT in the late stage could not be explained solely by this pathway, cooperation of another reaction mechanism, the cationic leaving group pathway, was proposed to rationalize the rate acceleration.

sym-triazine derivatives. 2. Synthesis, properties, and structure of 2-oxo-1,2-dihydro-sym-triazines

Previously unreported 2-oxo-1,2-dihydro-sym-triazines have been prepared and their alkylation reactions have been studied. It was found that, independently of the structure and nature of the substituent in positions 4 and 6 of the triazine ring or the str

A Simple Practical Method for the Synthesis of 4,6-Dimethoxy-1,3,5-triazin- 2(1H)-one Using Dimethylamine-Functionalized Solid-Phase Reagents

A simple practical method for the synthesis of 4,6-dimethoxy-1,3,5-triazin- 2(1H)-one was developed. The desired product was easily obtained from 2-chloro-4,6-dimethoxy-1,3,5-tri-azine and acetic acid by shaking with dimethylamine-functionalized silica ge

Triazine-Based Cationic Leaving Group: Synergistic Driving Forces for Rapid Formation of Carbocation Species

A new triazine-based cationic leaving group has been developed for the acid-catalyzed alkylation of O- and C-nucleophiles. There are two synergistic driving forces, namely, stable C=O bond formation and charge-charge repulsive effects, involved in the rapid generation of the carbocation species in the presence of trifluoromethanesulfonic acid (～200 mol %). Considerable rate acceleration of benzylation, allylation, and p-nitrobenzylation was observed as compared to the reactions with less than 100 mol % of the acid catalyst. The triazine-based leaving group showed superior p-nitrobenzylation yield and stability in comparison to common leaving groups, trichloroacetimidate and bromide. A plausible reaction mechanism (the cationic leaving group pathway) was proposed on the basis of mechanistic and kinetic studies, NMR experiments, and calculations.

USE OF A L,3J5-TRIAZIN-2-YL PHOSPHORAMIDATE COMPOUND IN THE SYNTHESIS OF SOFOSBUVIR

The present invention relates to a new type of 1,3.5-triazin-2-yl phosphoramidates of general formula I with the absolute configuration (S) at the phosphorus atom, an Sp diastereoisomer, wherein R1 and R2 can independently be H, a C1-C6 (un)branched alkyl, a C1-C6 (un)branched alkoxy group, a C1-C6 (un)branched alkylsulfanyl group, C1-C6 (un)branched monoalkylamino or dialkylamino group, including cyclic amino groups, e.g. pyrrolidino, piperidino or morpholino group; and to their use for the production of biologically active phosphoramidate prodrugs, especially sofosbuvir of formula II. Sofosbuvir II is a nucleotide inhibitor of the RNA polymerase, used for the treatment of hepatitis C in the form of a prodrug, releasing the active antiviral agent 2'-deoxy-2'-a-fluoro- P-C-methyluridine-5'-triphosphate in the organism.

Privilege Ynone Synthesis via Palladium-Catalyzed Alkynylation of "Super-Active Esters"

A neat palladium-catalyzed alkynylation reaction was developed with "super-active ester" as the carbonyl electrophile, which provides a clean and efficient synthetic protocol for a broad array of ynone compounds under CO-, Cu-, ligand-, and base-free conditions. The superior activity of triazine ester was rationalized by the strong electron-withdrawing ability and the unique affinity of triazine on palladium. A mechanistic experiment clearly demonstrated that the N-Pd coordination of triazine plays a crucial role for the highly efficient C-O activation. (Chemical Equation presented).

Study of the Reactivities of Acid-Catalyzed O-Benzylating Reagents Based on Structural Isomers of 1,3,5-Triazine

We have demonstrated O-benzylating abilities of both 4,6-bis(benzyloxy)-1,3,5-triazin-2(1H)-one (DiBOT) and 6-(benzyloxy)-1,3,5-triazine-2,4(1H,3H)-dione (MonoBOT), which have been previously suggested as reaction intermediates of the acid-catalyzed benzylation of 2,4,6-tris(benzyloxy)-1,3,5-triazine (TriBOT). We studied the effect on the reactivity of acid-catalyzed O-benzylation caused by the isomeric core triazine structures in these compounds by carrying out a kinetic study and estimating relative basicities using model compounds. Since MonoBOT showed superior reactivity, 1,3,5-triazine-2,4(1H,3H)-dione is a promising core structure for acid-catalyzed alkylating reagents.