1132659-97-2

Upstream product

• 584-02-1 2-pentanol 
• 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 
• 138-59-0 shikimic acid 
• 101769-63-5 (3R,4S,5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid ethyl ester 
• 1132659-94-9 (3R,4S,5R)-3,4,5-tris-methanesulfonyloxy-cyclohex-1-enecarboxylic acid ethyl ester 
• 1151665-75-6 (3R,4S,5R)-3-azido-4,5-bis-methanesulfonyloxy-cyclohex-1-enecarboxylic acid ethyl ester 
• 122-52-1 triethyl phosphite 

Downstream Products

• 1132660-00-4 (3R,4R,5S)-5-azido-4-(diethoxy-phosphorylamino)-3-(1-ethyl-propoxy)-cyclohex-1-enecarboxylic acid ethyl ester 
• 1132659-98-3 (3R,4S,5R)-4-amino-3-(1-ethyl-propoxy)-5-methanesulfonyloxy-cyclohex-1-enecarboxylic acid ethyl ester 
• 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 
• 1588477-10-4 ethyl (3R,4R,5S)-4-acetamido-5-(1-(benzyloxycarbonyl)-2-ethylguanidino)-3-(pentan-3-yloxy)-cyclohex-1-enecarboxylate 
• 1588477-11-5 ethyl (3R,4R,5S)-4-acetamido-5-(1-(benzyloxycarbonyl)-2-propylguanidino)-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate 
• 1588477-12-6 ethyl (3R,4R,5S)-4-acetamido-5-(1-(benzyloxycarbonyl)-2-isopropylguanidino)-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate 
• 1588477-13-7 ethyl (3R,4R,5S)-4-acetamido-5-(1-(benzyloxycarbonyl)-2-cyclopropylguanidino)-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate 
• 1588477-14-8 ethyl (3R,4R,5S)-4-acetamido-5-(2-allyl-1-(benzyloxycarbonyl)guanidino)-3-(pentan-3-yloxy)-cyclohex-1-enecarboxylate 
• 1588477-15-9 ethyl (3R,4R,5S)-4-acetamido-5-(1-(benzyloxycarbonyl)-2-(2,2,2-trifluoroethyl)guanidino)-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate 
• 1588489-21-7 (3R,4R,5S)-4-acetamido-5-((E)-2-methylguanidino)-3-(pentan-3-yloxy)cyclohex-1-enecarboxylic acid trifluoroacetate 
• 1588489-22-8 (3R,4R,5S)-4-acetamido-5-((E)-2-ethylguanidino)-3-(pentan-3-yloxy)cyclohex-1-enecarboxylic acid trifluoroacetate 

Relevant academic research and scientific papers

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%.

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.

Method for preparing oseltamivir phosphate by azide process

The invention belongs to the field of pharmaceutical chemicals, and particularly relates to a method for preparing oseltamivir phosphate by an azide process. The method comprises the following steps:reacting a compound shown in a formula (III) with sodium azide and ammonium chloride, opening a nitrogen heterocyclic ring, performing acetylation, reducing an azide group, removing tert-butyl, salifying with phosphoric acid, and purifying to obtain pure oseltamivir phosphate shown in a formula (I). According to the method, diallylamine with strong corrosivity and expensive palladium acetate do not need to be used so that the enterprise cost is reduced.

Oseltamivir analogues bearing N-substituted guanidines as potent neuraminidase inhibitors

A series of oseltamivir analogues bearing an N-substituted guanidine unit were prepared and evaluated as inhibitors of neuraminidases from four strains of influenza the two most potent analogues identified contain relatively small N-guanidine substituents (N-methyl and N-hydroxyl) and display enhanced inhibition with IC50 values in the low nanomolar range against neuraminidases from wild-type and oseltamivir-resistant strains. Potential advantages of including the N-hydroxyguanidine moiety in neuraminidase inhibitors are also discussed.

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.