221387-17-3

Upstream product

• 221386-97-6 (4aR,6R,8aS)-6-Hydroxy-2,3-dimethoxy-2,3-dimethyl-8-oxo-octahydro-benzo[1,4]dioxine-6-carboxylic acid methyl ester 
• 221386-99-8 (4aR,6S,8aR)-8-But-(E)-ylidene-2,3-dimethoxy-2,3-dimethyl-6-triethylsilanyloxy-octahydro-benzo[1,4]dioxine-6-carboxylic acid methyl ester 
• 221387-00-4 (4aR,6S,8R,8aR)-8-Butyl-2,3-dimethoxy-2,3-dimethyl-6-triethylsilanyloxy-octahydro-benzo[1,4]dioxine-6-carboxylic acid methyl ester 
• 221386-98-7 (4aR,6S,8aR)-8-But-(E)-ylidene-6-hydroxy-2,3-dimethoxy-2,3-dimethyl-octahydro-benzo[1,4]dioxine-6-carboxylic acid methyl ester 
• 221387-01-5 (4aR,6S,8R,8aR)-8-Butyl-6-hydroxy-2,3-dimethoxy-2,3-dimethyl-octahydro-benzo[1,4]dioxine-6-carboxylic acid methyl ester 
• 221387-02-6 (4aR,8R,8aR)-8-Butyl-2,3-dimethoxy-2,3-dimethyl-2,3,4a,5,8,8a-hexahydro-benzo[1,4]dioxine-6-carboxylic acid methyl ester 
• 221387-12-8 (3R,4S,5S)-4-Amino-5-azido-3-butyl-cyclohex-1-enecarboxylic acid methyl ester 
• 221387-06-0 (1S,5R,6R)-5-Butyl-7-oxa-bicyclo[4.1.0]hept-3-ene-3-carboxylic acid methyl ester 
• 221387-11-7 (1R,5R,6S)-5-Butyl-7-aza-bicyclo[4.1.0]hept-3-ene-3-carboxylic acid methyl ester 
• 221387-03-7 (3R,4R,5R)-3-Butyl-4,5-dihydroxy-cyclohex-1-enecarboxylic acid methyl ester 
• 221387-14-0 (3R,4S,5S)-4-Acetylamino-5-azido-3-butyl-cyclohex-1-enecarboxylic acid methyl ester 

Relevant academic research and scientific papers

C3-thia and C3-carba isosteres of a carbocyclic influenza neuraminidase inhibitor, (3R,4R,5S).4-acetamido-5-amino-3-propoxy-1-cyclohexene-1-carboxylic acid

The importance of the oxygen atom in the C3 ether side chain of a carbocyclic influenza neuraminidase inhibitor 3 was investigated by replacement of the C3 ether oxygen atom of 3 with either a sulfur atom (compound 4) or a carbon atom (compound 5). The regio- and stereospecific syntheses of both isoteres are described starting from (-)-quinic acid.