949962-56-5

Basic information

• Product Name: (3R,4R,5S)-4-acetamido-5-amino-3-(1-ethylpropoxy)cyclohex-1-ene-1-phosphonic acid
• Synonyms: (3R,4R,5S)-4-acetamido-5-amino-3-(1-ethylpropoxy)cyclohex-1-ene-1-phosphonic acid
• CAS NO: 949962-56-5
• Molecular Weight: 320.326
• Mol File: 949962-56-5.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: (3R,4R,5S)-4-acetamido-5-amino-3-(1-ethylpropoxy)cyclohex-1-ene-1-phosphonic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,4R,5S)-4-acetamido-5-amino-3-(1-ethylpropoxy)cyclohex-1-ene-1-phosphonic acid(949962-56-5)
• EPA Substance Registry System: (3R,4R,5S)-4-acetamido-5-amino-3-(1-ethylpropoxy)cyclohex-1-ene-1-phosphonic acid(949962-56-5)

Safety Data

• Hazardous Substances Data: 949962-56-5(Hazardous Substances Data)

Upstream product

• 950478-34-9 diethyl (3R,4R,5S)-4-acetamido-5-amino-3-(1-ethylpropoxy)-1-cyclohexene-1-phosphonate 
• 1062100-87-1 diethyl (3R,4R,5S)-4-acetamido-5-tert-butoxycarbonylamino-3-(1-ethylpropoxy)cyclohex-1-ene-1-phosphonate 
• 764639-63-6 (3R,4R,5S)-4-acetamido-5-[(tert-butoxycarbonyl)-amino]-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylic acid 
• 367252-68-4 (3R,4R,5S)-ethyl 4-acetamido-5-((tert-butoxycarbonyl)amino)-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate 
• 196618-13-0 oseltamivir 
• 204255-11-8 oseltamivir phosphate 
• 1062100-84-8 (3R,4R,5S)-4-acetamido-5-[(tert-butoxycarbonyl)-amino]-3-(1-ethylpropoxy)-1-bromocyclohexene 

Relevant articles and documents

Kinetic, thermodynamic and structural analysis of tamiphosphor binding to neuraminidase of H1N1 (2009) pandemic influenza

Influenza virus causes severe respiratory infections that are responsible for up to half a million deaths worldwide each year. Two inhibitors targeting viral neuraminidase have been approved to date (oseltamivir, zanamivir). However, the rapid development of antiviral drug resistance and the efficient transmission of resistant viruses among humans represent serious threats to public health. The approved influenza neuraminidase inhibitors have (oxa)cyclohexene scaffolds designed to mimic the oxonium transition state during enzymatic cleavage of sialic acid. Their active forms contain a carboxylate that interacts with three arginine residues in the enzyme active site. Recently, the phosphonate group was successfully used as an isostere of the carboxylate in oseltamivir, and the resulting compound, tamiphosphor, was identified as a highly active neuraminidase inhibitor. However, the structure of the complex of this promising inhibitor with neuraminidase has not yet been reported. Here, we analyzed the interaction of a set of oseltamivir and tamiphosphor derivatives with neuraminidase from the A/California/07/2009 (H1N1) influenza virus. We thermodynamically characterized the binding of oseltamivir carboxylate or tamiphosphor to the neuraminidase catalytic domain by protein microcalorimetry, and we determined crystal structure of the catalytic domain in complex with tamiphosphor at 1.8 ? resolution. This structural information should aid rational design of the next generation of neuraminidase inhibitors.

Synthesis of oseltamivir and tamiphosphor from N-acetyl-d-glucosamine

Using N-acetyl-d-glucosamine as a starting material, the anti-influenza drugs oseltamivir and tamiphosphor were synthesized via a pivotal intermediate of aldehyde 8. An intramolecular Horner-Wadsworth-Emmons reaction was utilized to construct the highly f

SYNTHESIS OF OSELTAMIVIR CONTAINING PHOSPHONATE CONGENERS WITH ANTI-INFLUENZA ACTIVITY

Novel phosphonate compounds are described. The compounds have activity as neuraminidase inhibitors against wild-type and H274Y mutant of H1N1 and H5N1 viruses. The present disclosure also provides an enantioselective synthetic route to known neuraminidase inhibitors oseltamivir and the anti-flu drug Tamiflu, as well as novel phosphonate compounds, via D-xylose. Another efficient and flexible synthesis of Tamiflu and the highly potent neuraminidase inhibitor Tamiphosphor was also achieved in 11 steps and > 20% overall yields from the readily available fermentation product (1S-cis)-3-bromo-3,5- cyclohexadiene-1,2-diol. Most of the reaction intermediates were obtained as crystals without tedious purification procedures. The key transformations include an initial regio- and stereoselective bromoamidation of a bromoarene cis- dihydrodiol, as well as the final palladium-catalyzed carbonylation and phosphonylation.