1122748-01-9

Basic information

• Product Name: C₁₆H₃₁N₄O₅P
• Synonyms: C₁₆H₃₁N₄O₅P
• CAS NO: 1122748-01-9
• Molecular Weight: 390.42
• Mol File: 1122748-01-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: C₁₆H₃₁N₄O₅P(CAS DataBase Reference)
• NIST Chemistry Reference: C₁₆H₃₁N₄O₅P(1122748-01-9)
• EPA Substance Registry System: C₁₆H₃₁N₄O₅P(1122748-01-9)

Safety Data

• Hazardous Substances Data: 1122748-01-9(Hazardous Substances Data)

Upstream product

• 949908-52-5 diethyl (3R,4R,5S)-4-acetamido-5-azido-3-hydroxy-1-cyclohexene-1-phosphonate 
• 949908-55-8 pentan-3-yl 2,2,2-trichloroacetimidate 
• 950478-34-9 diethyl (3R,4R,5S)-4-acetamido-5-amino-3-(1-ethylpropoxy)-1-cyclohexene-1-phosphonate 
• 1401808-94-3 C₁₈H₃₅N₄O₅P 
• 67451-62-1 cis-(1S,2S)-1,2-dihydroxy-3-bromocyclohexa-3,5-diene 
• 130669-75-9 (3aS,7aS)-4-bromo-2,2-dimethyl-3a,7a-dihydro-1,3-benzodioxole 
• 1106677-14-8 N-[(3aR,4R,5S,7aS)-4,7-dibromo-2,2-dimethyl-3a,4,5,7a-tetrahydro-1,3-benzodioxol-5-yl]acetamide 
• 1056467-86-7 (3aS,4S,5S,7aS)-8-acetyl-7-bromo-2,2-dimethyl-3a,4,5,7a-tetrahydro-4,5-epimino-1,3-benzodioxole 
• 1062100-77-9 (1S,2R,5R,6S)-6-acetamido-2,3-dibromo-5-(1-ethylpropoxy)-cyclohex-3-en-1-yl acetate 
• 1122581-40-1 N-[(1R,2R,6R)-4-bromo-2-(1-ethylpropoxy)-6-hydroxycyclohex-3-en-1-yl]acetamide 
• 196618-13-0 oseltamivir 
• 367252-68-4 (3R,4R,5S)-ethyl 4-acetamido-5-((tert-butoxycarbonyl)amino)-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate 

Downstream Products

• 1122581-43-4 ethyl (3R,4R,5S)-4-acetamido-5-[N₂,N₃-bis(tert-butoxycarbonyl)guanidino]-3-(1-ethylpropoxy)-1-cyclohexene-1-phosphonate ammonium salt 

Relevant articles and documents

Tamiphosphor monoesters as effective anti-influenza agents

Oseltamivir is a potent neuraminidase inhibitor for influenza treatment. By replacing the carboxylate group in oseltamivir with phosphonate monoalkyl ester, a series of tamiphosphor derivatives were synthesized and shown to exhibit high inhibitory activities against influenza viruses. Our molecular modeling experiments revealed that influenza virus neuraminidase contains a 371-cavity near the S1-site to accommodate the alkyl substituents of tamiphosphor monoesters to render appreciable hydrophobic interactions for enhanced affinity. Furthermore, guanidino-tamiphosphor (TPG) monoesters are active to the oseltamivir-resistant mutant. TPG monohexyl ester 4e having a more lipophilic alkyl substituent showed better cell permeability and intestinal absorption than the corresponding monoethyl ester 4c, but both compounds showed similar bioavailability. Intranasal administration of TPG monoesters at low dose greatly improved the survival rate of mice infected with lethal dose of H1N1 influenza virus, whereas 4c provided better protection of the infected mice than oseltamivir and other phosphonate congeners by oral administration.

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.