1132659-98-3

Upstream product

• 138-59-0 shikimic acid 
• 1132659-96-1 (1S,5R,6S)-7-(diethoxy-phosphoryl)-5-methanesulfonyloxy-7-aza-bicyclo[4.1.0]hept-2-ene-3-carboxylic acid ethyl ester 
• 101769-63-5 (3R,4S,5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid ethyl ester 
• 584-02-1 2-pentanol 
• 1151665-75-6 (3R,4S,5R)-3-azido-4,5-bis-methanesulfonyloxy-cyclohex-1-enecarboxylic acid ethyl ester 
• 1132659-94-9 (3R,4S,5R)-3,4,5-tris-methanesulfonyloxy-cyclohex-1-enecarboxylic acid ethyl ester 
• 1401454-81-6 (2R,3S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-3-((R)-3-(ethoxycarbonyl)-1-hydroxybut-3-en-1-yl)aziridine-1-carboxylate 
• 1401454-88-3 ethyl (3R,4S,5R)-4-(tert-butoxycarbonylamino)-3-(1-ethylpropoxy)-5-(methanesulfonyloxy)cyclohex-1-ene-1-carboxylate 
• 1401454-87-2 ethyl (1S,5R,6S)-7-(tert-butoxycarbonyl)-5-(methanesulfonyloxy)-7-azabicyclo[4.1.0]hept-2-ene-3-carboxylate 
• 1401454-86-1 tert-butyl (2S,3S)-2-ethenyl-3-{(1R)-3-(ethoxycarbonyl)-1-[(methylsulfonyl)oxy]but-3-en-1-yl}aziridine-1-carboxylate 
• 1401454-85-0 (2S,3R)-tert-butyl 2-((R)-3-(ethoxycarbonyl)-1-(methanesulfonyloxy)but-3-en-1-yl)-3-formylaziridine-1-carboxylate 
• 1401454-84-9 C₁₆H₂₇NO₈S 
• 1401454-83-8 (2R,3S)-1-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-3-((R)-3-(ethoxycarbonyl)-1-(methanesulfonyloxy)but-3-en-1-yl)-aziridine-1-carboxylate 
• 1132659-97-2 (3R,4S,5R)-4-[(diethoxyphosphoryl)amino]-3-(1-ethylpropoxy)-5-(methanesulfonyloxy)cyclohex-1-enecarboxylic acid ethyl ester 

Downstream Products

• 1402431-91-7 ethyl (3R,4R,5R)-4-acetylamino-5-amino-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate 
• 204255-11-8 oseltamivir phosphate 
• 196618-13-0 oseltamivir 
• 1132659-99-4 (3R,4S,5R)-4-acetylamino-3-(1-ethyl-propoxy)-5-methanesulfonyloxy-cyclohex-1-enecarboxylic acid ethyl ester 
• 204255-06-1 oseltamivir 

Relevant academic research and scientific papers

FLOW SYNTHESIS PROCESS FOR THE PRODUCTION OF OSELTAMIVIR

This invention provides for a flow synthesis process for producing Oseltamivir and pharmaceutically acceptable salts thereof from shikimic acid in particular but not exclusively to a flow synthesis process for producing Oseltamivir phosphate from shikimic acid in a nine-step flow synthesis that provides for superior reaction times and product yields compared to known methods.

Facile method for the synthesis of oseltamivir phosphate

A ten-step scheme for the preparation of an antiviral agent, ethyl (3R,4R,5S)-4-acetylamino-5-amino-3-(pent-3-yloxy)cyclohex-1-enecarboxylate phosphate, from (-)-shikimic acid was studied. The main parameters of the synthesis were determined and the optimal conditions for the preparation of the intermediate compounds were selected. The total yield of oseltamivir phosphate calculated based on (-)-shikimic acid was 27%.

Synthesis of (-)-oseltamivir phosphate (tamiflu) starting from cis-2,3-bis(hydroxymethyl)aziridine

Oseltamivir phosphate (Tamiflu) has been synthesized from cis-2,3-bis(hydroxymethyl)aziridine. After protection of the cis-2,3-bis(hydroxymethyl)aziridine with a Boc group, desymmetrization provided a chiral aziridine, which was a key intermediate to install the required stereogenic center containing a nitrogen atom. Allylation and ring closing metathesis are the key reactions to obtain the cyclic product that was successfully converted to the desired oseltamivir phosphate.

Preparation of oseltamivir phosphate

The invention provides a new process for the conversion of shikimic acid to oseltamivir (I), and optionally to an acid addition salt, via the intermediate phosphoramide VII.