367252-65-1

Upstream product

• 1122-58-3 dmap 
• 24424-99-5 di-tert-butyl dicarbonate 
• 367252-71-9 (3aS,5R,6R,7R,7aS)-7-(1-ethylpropoxy)-6-hydroxy-2-oxooctahydrobenzooxazole-5-carboxylic acid ethyl ester 
• 1393086-01-5 C₂₅H₃₇O₉P 
• 943515-58-0 (3aR,7R,7aS)-ethyl 2,2-diethyl-7-hydroxy-3a,6,7,7a-tetrahydrobenzo[d][1,3]dioxole-5-carboxylate 
• 1234286-93-1 (3aR,7aS)-ethyl 2,2-diethyl-7-(hydroxyimino)-3a,6,7,7a-tetrahydrobenzo[d][1,3]dioxole-5-carboxylate 
• 1234286-95-3 ethyl 3,4-O-isopentylidene-5-oxo shikimate 
• 1234287-00-3 ethyl (3R,4S,5S)-3-(1-ethylpropoxy)-4-hydroxy-5-amino-cyclohex-1-ene-1-carboxylate 

Downstream Products

• 367252-66-2 (3R,4S,5S)-5-tert-butoxycarbonylamino-3-(1-ethylpropoxy)-4-trifluoromethanesulfonyloxycyclohex-1-enecarboxylic acid ethyl ester 
• 367252-67-3 (3R,4R,5S)-4-azido-5-tert-butoxycarbonylamino-3-(1-ethylpropoxy)cyclohex-1-enecarboxylic acid ethyl ester 
• 367252-68-4 (3R,4R,5S)-ethyl 4-acetamido-5-((tert-butoxycarbonyl)amino)-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate 
• 204255-11-8 oseltamivir phosphate 

Relevant academic research and scientific papers

A concise and practical synthesis of oseltamivir phosphate(Tamiflu) from d-mannose

A short and practical synthesis of oseltamivir phosphate was accomplished in 11 steps from inexpensive and abundant starting material, d-mannose. This synthetic route featured an intramolecular Horner-Wadsworth-Emmons reaction as the key step to furnish the cyclohexene ring product. The hydroxyl group was converted stereo specifically into an amino group by oxidation to the ketone and reductive amination whereas the second amino group was introduced by azide substitution of a hydroxyl group. This synthesis provided an economical and practical alternative for the synthesis of Tamiflu.

An efficient synthesis of oseltamivir phosphate (Tamiflu) via a metal-mediated domino reaction and ring-closing metathesis

An efficient synthesis of the influenza neuraminidase inhibitor prodrug oseltamivir phosphate (Tamiflu) from cheap, commercially available d-ribose is described. The main features of this approach comprise a metal (Zn, In)-mediated domino reaction and ring-closing olefin metathesis (RCM) of the resultant functionalized dienes to produce the Tamiflu skeleton. The synthesis described in this Letter represents a new and efficient transformation of a shikimic acid derivative into a 1,2-diamino compound which involved oxidation of an alcohol followed by reductive amination, regioselective ring opening of an amino pentylidene ketal and stereospecific nucleophilic replacement of a triflate with an azide.

Stereo-specific synthesis of shimikic acid derivatives with improved efficiency

The invention provides a multistep synthesis for the preparation of 4,5-diamino shikimic acid derivatives of formula 1starting from an isophthalic acid derivative of formula 24,5-Diamino shikimic acid derivatives are potent inhibitors of viral neuraminidase.