1373702-86-3

Upstream product

• 49762-08-5 3-hydroxy-4-methylthiazole-2(3H)-thione 
• 764639-63-6 (3R,4R,5S)-4-acetamido-5-[(tert-butoxycarbonyl)-amino]-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylic acid 
• 24424-99-5 di-tert-butyl dicarbonate 
• 187227-45-8 oseltamivir acid 
• 204255-11-8 oseltamivir phosphate 
• 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

• 1062100-84-8 (3R,4R,5S)-4-acetamido-5-[(tert-butoxycarbonyl)-amino]-3-(1-ethylpropoxy)-1-bromocyclohexene 
• 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 
• 1616376-26-1 mono(3-phenylpropyl) (3R,4R,5S)-4-acetamido-3-(1-ethylpropoxy)-5-guanidino-1-cyclohexene-1-phosphonate 
• 1616376-25-0 monohexyl (3R,4R,5S)-4-acetamido-3-(1-ethylpropoxy)-5-guanidino-1-cyclohexene-1-phosphonate 
• 1616376-23-8 monobutyl (3R,4R,5S)-4-acetamido-3-(1-ethylpropoxy)-5-guanidino-1-cyclohexene-1-phosphonate 
• 1616376-32-9 mono[(1H-3-indol-3-yl)propyl] (3R,4R,5S)-4-acetamido-5-amino-3-(1-ethylpropoxy)-1-cyclohexene-1-phosphonate 
• 1616376-30-7 mono(3-phenylprop-1-yl) (3R,4R,5S)-4-acetamido-5-amino-3-(1-ethylpropoxy)-1-cyclohexene-1-phosphonate 
• 1616376-29-4 monobutyl (3R,4R,5S)-4-acetamido-5-amino-3-(1-ethylpropoxy)-1-cyclohexene-1-phosphonate 
• 1616373-96-6 di(3-phenylprop-1-yl) (3R,4R,5S)-4-acetamido-5-[N²,N³-bis(tert-butoxycarbonyl)guanidino]-3-(1-ethylpropoxy)-1-cyclohexene-1-phosphonate 
• 1616373-95-5 dihexyl (3R,4R,5S)-4-acetamido-5-[N²,N³-bis(tert-butoxycarbonyl)guanidino]-3-(1-ethylpropoxy)-1-cyclohexene-1-phosphonate 
• 1616373-94-4 dibutyl (3R,4R,5S)-4-acetamido-5-[N²,N³-bis(tert-butoxycarbonyl)guanidino]-3-(1-ethylpropoxy)-1-cyclohexene-1-phosphonate 
• 1616373-93-3 di[3-(1H-indol-3-yl)propyl] (3R,4R,5S)-4-acetamido-5-tert-butoxycarbonylamino-3-(1-ethylpropoxy)-1-cyclohexene-1-phosphonate 
• 1616373-92-2 di(3-phenylprop-1-yl) (3R,4R,5S)-4-acetamido-5-tert-butoxycarbonylamino-3-(1-ethylpropoxy)-1-cyclohexene-1-phosphonate 

Relevant academic research and scientific papers

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.

Formal synthesis of tamiflu: Conversion of tamiflu into tamiphosphor

A short, enantiomeric, synthesis of Shibasakis 3rd generation intermediate to form (-)-oseltamivir phosphate (Tamiflu) has been achieved in eight steps with the use of inexpensive starting materials. A formal synthetic route to convert tamiflu into tamiphosphor via Fangs tamiphosphor intermediate has been accomplished. Georg Thieme Verlag Stuttgart · New York.