130712-01-5Relevant academic research and scientific papers
Olivanic Acid Analogues. Part 5. Synthesis of 3-Alkylthio and 3-Alkylsulphinyl Analogues via Michael Addition of Thiols to 3-Unsubstituted 1-Azabicyclohept-2-ene-2-carboxylates. X-Ray Molecular Structure of (2RS,3RS,5SR)-Benzyl 3-Ethylthio-7-oxo-1-azabicycloheptane-2-car...
Bateson, John H.,Roberts, Patricia M.,Smale, Terence C.,Southgate, Robert
, p. 1541 - 1553 (2007/10/02)
Reaction of thiols with 1-azabicyclohept-2-ene-2-carboxylates results in Michael addition to the double bond, producing in high yield 2-thio-substituted 1-azabicycloheptane-2-carboxylates; the major products such as the ethylthio adducts (5) and (7) are those of trans-addition to the double bond.Oxidation of these major adducts with iodobenzene dichloride in the presence of aqueous pyridine results in highly regio- and stereo-specific oxidation to α-chlorosulphoxides as in compounds (27) and (28); base-catalysed elimination produces the Δ2-unsaturated α- and β-sulphoxides (31) and (32).Oxidation of the thiol addition products with iodobenzene dichloride-pyridine under anhydrous conditions gives the Δ3-unsaturated isomers such as (35) and (36) rather than the α-chloro sulphide products; equilibration with base results in a mixture of the Δ3- and Δ2-isomers which can be separated.Deprotection gives the bioactive Δ2-sodium salts , while the corresponding Δ3-salts (38) and (39) show no antibacterial properties.
