1173701-22-8

Upstream product

• 93-89-0 benzoic acid ethyl ester 
• 64-17-5 ethanol 
• 201230-82-2 carbon monoxide 
• 138769-92-3 cis-(1S,2S)-1,2-dihydroxy-3-iodocyclohexa-3,5-diene 

Downstream Products

• 1185040-36-1 C₉H₁₄O₄ 
• 1349901-46-7 C₂₁H₃₂N₂O₇S 
• 1196491-13-0 ethyl (3R,4R,5S)-5-((tert-butoxycarbonyl)amino)-3-hydroxy-4-(4-methylphenylsulfonamido)cyclohex-1-ene carboxylate 
• 1196491-09-4 ethyl (3aR,4R,6S,7R,7aS)-6-[(tert-butoxycarbonyl)amino]-2,2-dimethyl-7-{[(4-methylphenyl)sulfonyl]amino}hexahydro-1,3-benzodioxole-4-carboxylate 
• 1349901-43-4 C₁₉H₂₆N₂O₆S 
• 1196490-97-7 ethyl (3aR,6S,7R,7aS)-6-azido-2,2-dimethyl-7-{[(4-methylphenyl)sulfonyl]amino}-3a,6,7,7a-tetrahydro-1,3-benzodioxole-4-carboxylate 
• 1196490-93-3 ethyl (3aS,4R,5R,7aR)-2,2-dimethyl-8-[(4-methylphenyl)-sulfonyl]-3a,4,5,7a-tetrahydro-4,5-epimino-1,3-benzodioxole-7-carboxylate 
• 1196491-05-0 ethyl (3aR,6S,7R,7aS)-6-[(tert-butoxycarbonyl)amino]-2,2-dimethyl-7-{[(4-methylphenyl)sulfonyl]amino}-3a,6,7,7a-tetrahydro-1,3-benzodioxole-4-carboxylate 
• 1349901-44-5 (1R,3S,4R,5R)-ethyl 4-acetamido-3-amino-5-hydroxycyclohexanecarboxylate 
• 1224161-51-6 ethyl (3aR, 4R,6S,7R,7aS)-7-acetamido-6-amino-2,2-dimethylhexahydrobenzo[d][1,3]dioxole-4-carboxylate 
• 949908-51-4 ethyl (3R,4R,5S)-4-(acetylamino)-5-azido-3-hydroxycyclohex-1-ene-1-carboxylate 
• 1137726-89-6 ethyl (3R,4R,5S)-4-acetylamino-5-tert-butoxycarbonylamino-3-hydroxy-cyclohex-1-enecarboxylate 
• 1224161-53-8 ethyl (1R,3S,4R,5R)-4-acetamido-3-(tert-butoxycarbonylamino)-5-hydroxycyclohexanecarboxylate 
• 1224161-52-7 (3aR,6S,7R,7aS)-7-acetylamino-6-tert-butoxycarbonylamino-2,2-dimethyl-3a,6,7,7a-tetrahydrobenzo[1,3]dioxole-4-carboxylic acid ethyl ester 

Relevant academic research and scientific papers

Palladium-catalyzed carbonylation of halo arene-cis-dihydrodiols to the corresponding carboxylates. Access to compounds unavailable by toluene dioxygenase-mediated dihydroxylation of the corresponding benzoate esters

A series of arene-cis-dihydrodiol carboxylates was prepared by palladium-catalyzed carbonylation of (1S, 2S-cis)-3-iodo-3,5-cyclohexadiene-1,2-diol, which is obtained in high titers by enzymatic dihydroxylation of iodobenzene. Both the free diol and the corresponding acetonide were subjected to this protocol to produce various arene-cis-dihydrodiol carboxylates that are unavailable by fermentation of the corresponding benzoates or are produced in low yields. The comparison of yields obtained from fermentation versus carbonylation was made for all compounds investigated. Experimental and spectral data are provided for all new compounds. This journal is

PROCESS AND COMPOUNDS FOR THE MANUFACTURE OF OSELTAMIVIR AND ANALOGS THEREOF, AND NEW ANTIVIRAL AGENTS

The present application relates to processes for the preparation of intermediates useful in the manufacture of oseltamivir and the H3PO4 salt of oseltamivir, Tamiflu?. The application further relates to novel intermediate and compoun

Short chemoenzymatic azide-free synthesis of oseltamivir (tamiflu): Approaching the potential for process efficiency

A short chemoenzymatic and azide-free synthesis of oseltamivir was attained with the key steps consisting of a one-pot Dauben-Michno oxidative transposition and animation and a reductive transposition of an acrylate.

Investigation of steric and functionality limits in the enzymatic dihydroxylation of benzoate esters. Versatile intermediates for the synthesis of pseudo-sugars, amino cyclitols, and bicyclic ring systems

A series of benzoate esters (methyl, ethyl, n-Pr, i-Pr, n-Bu, t-Bu, allyl, and propargyl) were subjected to enzymatic dihydroxylation by E. coli JM 109(pDTG 601) strain in a whole-cell fermentation. The cis-cyclohexadienediols were obtained in yields of ～1g/L except for n-propyl- and i-propyl benzoate which were found to be poor substrates. n-Butyl and t-butyl benzoates were not oxidized at all. The absolute stereochemistry for all metabolites was determined by comparison with a standard prepared from (1S-cis)-3-bromo-3,5- cyclohexadiene-1,2-diol, whose absolute configuration is well established. The free diols were found to be quite stable compared to other cis-dihydrodiols of this type, however, their acetonides underwent a dimerization via a regio- and stereoselective Diels-Alder cycloaddition. The diol derived from ethyl benzoate was subjected to a stereo- and regioselective inverse electron demand Diels-Alder cycloadditions with several dienophiles. The new adducts were completely characterized. The hetero-Diels-Alder reaction of this diol with an acyl nitroso dienophile yielded regio- and stereoselectively a bicyclic oxazine, which upon reduction provided a useful derivative of amino shikimate that can be exploited in an approach to oseltamivir (Tamiflu) and other amino cyclitols. The diol was also converted to carba-α-L-galactopyranose to demonstrate its potential utility as a source of pseudo sugars. Experimental and spectral data are provided for all new compounds. The Royal Society of Chemistry 2009.