1132659-94-9

Basic information

• Product Name: (3R,4S,5R)-3,4,5-tris-methanesulfonyloxy-cyclohex-1-enecarboxylic acid ethyl ester
• Synonyms: (3R,4S,5R)-3,4,5-tris-methanesulfonyloxy-cyclohex-1-enecarboxylic acid ethyl ester
• CAS NO: 1132659-94-9
• Molecular Weight: 436.482
• Mol File: 1132659-94-9.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: (3R,4S,5R)-3,4,5-tris-methanesulfonyloxy-cyclohex-1-enecarboxylic acid ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,4S,5R)-3,4,5-tris-methanesulfonyloxy-cyclohex-1-enecarboxylic acid ethyl ester(1132659-94-9)
• EPA Substance Registry System: (3R,4S,5R)-3,4,5-tris-methanesulfonyloxy-cyclohex-1-enecarboxylic acid ethyl ester(1132659-94-9)

Safety Data

• Hazardous Substances Data: 1132659-94-9(Hazardous Substances Data)

Upstream product

• 158341-64-1 (3R,4S,5S)-3,4,5-trihydroxycyclohex-1-enecarboxylic acid 
• 124-63-0 methanesulfonyl chloride 
• 138-59-0 shikimic acid 
• 101769-63-5 (3R,4S,5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid ethyl ester 

Downstream Products

• 1151665-75-6 (3R,4S,5R)-3-azido-4,5-bis-methanesulfonyloxy-cyclohex-1-enecarboxylic acid ethyl ester 
• 204255-06-1 oseltamivir 
• 1132659-99-4 (3R,4S,5R)-4-acetylamino-3-(1-ethyl-propoxy)-5-methanesulfonyloxy-cyclohex-1-enecarboxylic acid ethyl ester 
• 1132659-97-2 (3R,4S,5R)-4-[(diethoxyphosphoryl)amino]-3-(1-ethylpropoxy)-5-(methanesulfonyloxy)cyclohex-1-enecarboxylic acid ethyl ester 
• 582-33-2 3-aminobenzoic acid ethyl ester 
• 1132659-98-3 (3R,4S,5R)-4-amino-3-(1-ethyl-propoxy)-5-methanesulfonyloxy-cyclohex-1-enecarboxylic acid ethyl ester 
• 196618-13-0 oseltamivir 
• 204255-11-8 oseltamivir phosphate 
• 56423-50-8 3-azido benzoic acid ethyl ester 
• 1070663-96-5 ethyl 3-((methylsulfonyl)oxy)benzoate 
• 1588477-09-1 ethyl (3R,4R,5S)-4-acetamido-5-(1-(benzyloxycarbonyl)-2-methylguanidino)-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate 
• 1588477-08-0 (3R,4R,5S)-ethyl 4-acetamido-5-(3-((benzyloxy)carbonyl)thioureido)-3-(pentan-3-yloxy)-cyclohex-1-enecarboxylate 
• 1192537-55-5 (3R,4R,5S)-5-[[(1Z)-[[(tert-butoxy)carbonyl]amino]([[(tert-butoxy)carbonyl]imino])methyl]amino]-4-acetylamino-3-(pent-3-yloxy)cyclohexyl-1-ene-1-carboxylic acid 

Relevant articles and documents

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.

The hydrophobic side chain of oseltamivir influences type A subtype selectivity of neuraminidase inhibitors

Neuraminidase, which plays a critical role in the influenza virus life cycle, is a target for new therapeutic agents. The study of structure–activity relationships revealed that the C-5 position amino group of oseltamivir was pointed to 150-cavity of the neuraminidase in group 1. This cavity is important for selectivity of inhibitors against N1 versus N2 NA. A serial of influenza neuraminidase inhibitors with the oseltamivir scaffold containing lipophilic side chains at the C-5 position have been synthesized and evaluated for their influenza neuraminidase inhibitory activity and selectivity. The results indicated that compound 13o (H5N1 IC50?=?0.1?±?0.04?μm, H3N2 IC50?=?0.26?±?0.18?μm) showed better inhibitory activity and selectivity against the group 1 neuraminidase. This study may provide a clue to design of better group 1 neuraminidase inhibitors.

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.