950478-34-9

Basic information

• Product Name: diethyl (3R,4R,5S)-4-acetamido-5-amino-3-(1-ethylpropoxy)-1-cyclohexene-1-phosphonate
• Synonyms: diethyl (3R,4R,5S)-4-acetamido-5-amino-3-(1-ethylpropoxy)-1-cyclohexene-1-phosphonate
• CAS NO: 950478-34-9
• Molecular Weight: 376.433
• Mol File: 950478-34-9.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: diethyl (3R,4R,5S)-4-acetamido-5-amino-3-(1-ethylpropoxy)-1-cyclohexene-1-phosphonate(CAS DataBase Reference)
• NIST Chemistry Reference: diethyl (3R,4R,5S)-4-acetamido-5-amino-3-(1-ethylpropoxy)-1-cyclohexene-1-phosphonate(950478-34-9)
• EPA Substance Registry System: diethyl (3R,4R,5S)-4-acetamido-5-amino-3-(1-ethylpropoxy)-1-cyclohexene-1-phosphonate(950478-34-9)

Safety Data

• Hazardous Substances Data: 950478-34-9(Hazardous Substances Data)

Upstream product

• 1062100-87-1 diethyl (3R,4R,5S)-4-acetamido-5-tert-butoxycarbonylamino-3-(1-ethylpropoxy)cyclohex-1-ene-1-phosphonate 
• 1373702-86-3 C₂₃H₃₅N₃O₆S₂ 
• 1062100-85-9 4-acetamido-5-(tert-butoxycarbonyl)amino-3-(1-ethylpropoxy)-1-iodo-1-cyclohexene 
• 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 
• 1122581-40-1 N-[(1R,2R,6R)-4-bromo-2-(1-ethylpropoxy)-6-hydroxycyclohex-3-en-1-yl]acetamide 

Downstream Products

• 949962-56-5 (3R,4R,5S)-4-acetamido-5-amino-3-(1-ethylpropoxy)cyclohex-1-ene-1-phosphonic acid 
• 1122748-00-8 C₁₅H₂₉N₂O₅P 
• 1401808-94-3 C₁₈H₃₅N₄O₅P 
• 949962-57-6 (3R,4R,5S)-4-acetamido-5-guanidino-3-(1-ethylpropoxy)-1-cyclohexene-1-phosphonic acid 
• 1122748-01-9 C₁₆H₃₁N₄O₅P 

Relevant articles and documents

A short synthetic pathway via three-component coupling reaction to tamiphosphor possessing anti-influenza activity

Three-component coupling reaction of (pent-3-oxy)acetaldehyde, (Z)-N-(2-nitrovinyl)acetamide, and tetraethyl 1,1-diylbis(phosphonate) is performed in a one-pot operation, followed by reduction of the nitro group and hydrolysis of the phosphonate ester, to afford 8.7% overall yield of tamiphosphor as a potent neuraminidase inhibitor with IC50 and EC50 values of 2.5 and 31.5 nM against wild-type H1N1 influenza virus. The tamiphosphor (5R)-epimer is a less active anti-influenza agent with IC50 and EC50 values of 39 and 117 nM.

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.