1151665-75-6

Basic information

• Product Name: (3R,4S,5R)-3-azido-4,5-bis-methanesulfonyloxy-cyclohex-1-enecarboxylic acid ethyl ester
• Synonyms: (3R,4S,5R)-3-azido-4,5-bis-methanesulfonyloxy-cyclohex-1-enecarboxylic acid ethyl ester
• CAS NO: 1151665-75-6
• Molecular Weight: 383.403
• Mol File: 1151665-75-6.mol
• Article Data: 11

Chemical Properties

• CAS DataBase Reference: (3R,4S,5R)-3-azido-4,5-bis-methanesulfonyloxy-cyclohex-1-enecarboxylic acid ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,4S,5R)-3-azido-4,5-bis-methanesulfonyloxy-cyclohex-1-enecarboxylic acid ethyl ester(1151665-75-6)
• EPA Substance Registry System: (3R,4S,5R)-3-azido-4,5-bis-methanesulfonyloxy-cyclohex-1-enecarboxylic acid ethyl ester(1151665-75-6)

Safety Data

• Hazardous Substances Data: 1151665-75-6(Hazardous Substances Data)

Upstream product

• 1350928-95-8 ethyl (3S,4R,5R)-3-azido-4,5-dihydroxycyclohex-1-ene-1-carboxylate 
• 124-63-0 methanesulfonyl chloride 
• 1132659-94-9 (3R,4S,5R)-3,4,5-tris-methanesulfonyloxy-cyclohex-1-enecarboxylic acid ethyl ester 
• 101769-63-5 (3R,4S,5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid ethyl ester 
• 138-59-0 shikimic acid 

Downstream Products

• 204255-11-8 oseltamivir phosphate 
• 196618-13-0 oseltamivir 
• 1132659-98-3 (3R,4S,5R)-4-amino-3-(1-ethyl-propoxy)-5-methanesulfonyloxy-cyclohex-1-enecarboxylic acid ethyl ester 
• 582-33-2 3-aminobenzoic acid ethyl ester 
• 1132659-97-2 (3R,4S,5R)-4-[(diethoxyphosphoryl)amino]-3-(1-ethylpropoxy)-5-(methanesulfonyloxy)cyclohex-1-enecarboxylic acid ethyl ester 
• 1132659-99-4 (3R,4S,5R)-4-acetylamino-3-(1-ethyl-propoxy)-5-methanesulfonyloxy-cyclohex-1-enecarboxylic acid ethyl ester 
• 204255-06-1 oseltamivir 
• 1191921-01-3 (3R,4R,5S)-4-acetylamino-5-acetylamino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylic acid ethyl ester 

Relevant articles and documents

Safe and highly efficient adaptation of potentially explosive azide chemistry involved in the synthesis of Tamiflu using continuous-flow technology

Tamiflu is one of the most effective anti-influenza drugs, which is currently manufactured by Hoffmann-La Roche from shikimic acid. Owing to its importance, more than 60 synthetic routes have been developed to date, however, most of the synthetic routes u

Continuous-Flow Synthesis of (-)-Oseltamivir Phosphate (Tamiflu)

Herein the anti-influenza drug (-)-oseltamivir phosphate is prepared in continuous flow from ethyl shikimate with 54% overall yield over nine steps and total residence time of 3.5 min from the individual steps. Although the procedure involved intermediate

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.