80044-10-6

Upstream product

• 106-89-8 epichlorohydrin 
• 70987-78-9 (S)-Glycidyl tosylate 
• 113826-06-5 (R)-glycidyl tosylate 
• 681225-50-3 (2S)-1-azido-3-chloropropan-2-ol 
• 3132-64-7 1,2-Epoxy-3-bromopropane 
• 51275-91-3 1-azido-3-chloro-propan-2-ol 

Downstream Products

• 124940-27-8 1-(oxiran-2-yl-methyl)-4-phenyl-1H-[1,2,3]-triazole 
• 124940-37-0 1-Oxiranylmethyl-5-phenyl-1H-[1,2,3]triazole 
• 124940-28-9 4-benzoyl-1-glycidyl-1,2,3-triazole 
• 88492-34-6 9-(3-azido-2-hydroxypropyl)adenine 
• 1429334-05-3 4-[4-{(R)-2-hydroxy-3-azidopropylamino}phenyl]morpholin-3-one 

Relevant academic research and scientific papers

Interrupted CuAAC-Thiolation for the Construction of 1,2,3-Triazole-Fused Eight-Membered Heterocycles from O-/N-Propargyl derived Benzyl Thiosulfonates with Organic Azides

A copper(I)-catalyzed interrupted click-sulfenylation of O-/N-propargyl benzyl thiosulfonates with organic azides has been disclosed. The unified CuAAC-thiolation provides a wide range of triazole-fused eight-membered heterocycles in good to high (51–94%) yields under mild reaction conditions. Moreover, a three-component reaction is also achieved involving O-/N-propargyl benzyl thiosulfonates, benzyl bromide, and sodium azide to deliver fused-triazoles in 61–74% yields. From a synthetic point of view, the present protocol has been demonstrated at gram-scale reactions. A plausible mechanism is also proposed based on experimental results and control experiments. (Figure presented.).

A GAP Replacement: Improved Synthesis of 3-Azidooxetane and Its Homopolymer Based on Sulfonic Acid Esters of Oxetan-3-ol

In the field of energetic binders, only hydroxy-terminated glycidyl azide polymer (GAP) has found widespread application and prevailed in the market. However, oxiranes such as glycidyl azide (GA) allow two ring-opening modes during polymerization and thus

Synthesis and cytotoxic activity of novel acyclic nucleoside analogues with functionality in click chemistry

We describe synthesis of novel acyclic nucleoside analogues which are building blocks for CuAAC reaction and their activity against two types of human cancer cell lines (HeLa, KB). Three of chosen compounds show promising cytotoxic activity. Synthesis pathway starting from simple and easily accessible substrates employing DMT or TBDPS protective groups is described. Adenosine and thymidine analogues containing alkyne moiety and adenosine analogue containing azido group were synthesized. The obtained units showed ability of forming triazole motif under the CuAAC reaction conditions.

The effect of glycidyl azide polymer on the stability and explosive properties of different interesting nitramines

Preparation of glycidyl azide polymer (GAP) and its influence on the stability and explosive properties of polymer bonded explosives (PBXs) based on several cyclic nitramines, namely β-1,3,5,7-tetranitro-1,3,5,7-tetrazocane (β-HMX), 1,3,5-trinitro-1,3,5-triazinane (RDX), ?-2,4,6,8,10,12-hexanitro-2,4,6,8,10,12-hexaazaisowurtzitane (?-CL-20) and cis-1,3,4,6-tetranitrooctahydroimidazo-[4,5-d]imidazole (BCHMX) are discussed. Impact and friction sensitivity were determined. Combustion heat and detonation velocity of the studied samples were measured. The detonation parameters were obtained by the EXPLO 5 thermodynamic code. The compatibility between the energetic polymeric matrix and the studied nitramines was discussed following a vacuum stability test. The relationship between performance and sensitivity was studied in comparison with literature HTPB compositions. The results showed that the GAP matrix increased both the detonation velocities of its PBXs by more than 500 m s-1 and the heat of explosion by nearly 1.13-1.16 times in comparison to PBXs based on HTPB for each individual explosive. The compatibility of BCHMX to the GAP matrix seems to be better than that of CL-20/GAP.

Halohydrin dehalogenase-catalysed transformations of epifluorohydrin

Biocatalytic ring-opening of epifluorohydrin has been performed by using halohydrin dehalogenase. The enzyme from Mycobacterium sp. GP1 (HheB2) catalysed reaction with high regioselectivity and low enantioselectivity in the presence of different nucleophi

FLUORESCENT BISPHOSPHONATE ANALOGS

Fluorescent probes based on N-heterocyclic bisphosphonates or their phosphonocarboxylate analogues are provided. The probes have variable spectroscopic properties, bone mineral binding affinities, and pharmacological activities. Methods for preparing the

Multivalent manganese complex decorated amphiphilic dextran micelles as sensitive MRI probes

T1 contrast agents based on Mn(ii) were conjugated on amphiphilic dextran micelles via click chemistry. The obtained paramagnetic nanomicelle contrast agent has a higher T1 relaxivity (13.3 Mn mmol-1 s-1) and better sensitivity than those of free Mn(ii) complexes. Studies carried out in vivo suggest that this contrast agent has a better and long-acting vascular enhancement effect at a lower manganese dosage (0.1 Mn mmol kg-1 BW). This journal is

Thermoresponsive xylan hydrogels via copper-catalyzed azide-alkyne cycloaddition

In the present work, hydrogels of birch wood xylan and thermoresponsive poly(ethylene glycol)-b-poly(propylene glycol)-b-poly(ethylene glycol) (PEG-PPG-PEG) were prepared using copper catalyzed alkyne-azide cycloaddition (CuAAC) in aqueous reaction conditions. First, reactive azide groups were introduced on the backbone of xylan by etherification of 1-azido-2,3- epoxypropane in alkaline water/isopropanol-mixture at ambient temperature, providing degree of substitution (DS) values up to 0.28. On the second step, the azide groups were reacted with propargyl bifunctional PEG-PPG-PEG utilizing CuAAC, leading to formation of crosslinked hydrogels. The novel xylan derivatives were characterized with liquid and solid state nuclear magnetic resonance spectroscopy (NMR), Fourier transform infrared spectroscopy (FT-IR) and elemental analysis (EA). The temperature controlled swelling behavior of the developed hydrogels was evaluated in the range of 7-70 C by water absorption and compressive stress-strain measurements, which showed a reduction in water content and change in stiffness with increasing temperature. The morphology of the hydrogels at different temperatures was studied by scanning electron microscopy (SEM), which showed a reduction in pore size with increasing temperature.

PROCESS FOR PREPARATION OF OXAZOLIDINONE DERIVATIVES

A process for preparation of oxazolidinone derivatives such as Linezolid and Rivaroxaban using (S)-Epichlorohydrin.

Transformations of 1-(oxiranylmethyl)-1,2,3-triazoles into 2-(Oxiranylmethyl)-1,2,3-triazoles and alkanenitriles

New reactions for the transformation of 1-(oxiranylmethyl)-1,2,3-triazoles into 2-(oxiranylmethyl)-1,2,3-triazoles or alkanenitriles were established. Successive treatment of the substrate with triflic acid and t-BuOH afforded 4,6-dihydro-5-hydroxy-1,3a,6a-triazapentalene derivative. Under the influence of NaH, the bicyclic compound was converted into a 2-(oxiranylmethyl)-1,2,3- triazole or an alkanenitrile. The reaction pathway depends on the substituent pattern of the epoxide side chain. Georg Thieme Verlag Stuttgart New York.