1132659-97-2

Basic information

• Product Name: (3R,4S,5R)-4-[(diethoxyphosphoryl)amino]-3-(1-ethylpropoxy)-5-(methanesulfonyloxy)cyclohex-1-enecarboxylic acid ethyl ester
• Synonyms: (3R,4S,5R)-4-[(diethoxyphosphoryl)amino]-3-(1-ethylpropoxy)-5-(methanesulfonyloxy)cyclohex-1-enecarboxylic acid ethyl ester
• CAS NO: 1132659-97-2
• Molecular Weight: 485.536
• Mol File: 1132659-97-2.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: (3R,4S,5R)-4-[(diethoxyphosphoryl)amino]-3-(1-ethylpropoxy)-5-(methanesulfonyloxy)cyclohex-1-enecarboxylic acid ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,4S,5R)-4-[(diethoxyphosphoryl)amino]-3-(1-ethylpropoxy)-5-(methanesulfonyloxy)cyclohex-1-enecarboxylic acid ethyl ester(1132659-97-2)
• EPA Substance Registry System: (3R,4S,5R)-4-[(diethoxyphosphoryl)amino]-3-(1-ethylpropoxy)-5-(methanesulfonyloxy)cyclohex-1-enecarboxylic acid ethyl ester(1132659-97-2)

Safety Data

• Hazardous Substances Data: 1132659-97-2(Hazardous Substances Data)

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 articles and documents

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.

Efficient access to oseltamivir phosphate (Tamiflu) via the O-trimesylate of shikimic acid ethyl ester

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