新产品编号:451379

Chemical Name: (+)-cis-6-Oxo-4-sulfanyl-1,4-azaphosphorinane-2-carboxylic acid P-oxide
CAS No. 217199-44-5 (cis-racemic)
项目整合开发状态: Biological Testing
项目研究机构: University of Sydney (Originator)
合成路线:Cyclization of amino acid (I) using 3-ethyl-1-(3-dimethylaminopropyl)carbodiimide (EDC) at a pH of 5.6 produced the azaphosphorinane (II) as a mixture of diastereoisomers.Subsequent reaction of (II) with diphenyldiazomethane yielded the bis(benzhydryl) ester (III) as a mixture of isomers,which were separable by column chromatography.Further refluxing of either isomer in EtOH removed selectively the phosphinic ester to give (IV) as an isomeric mixture.Coupling of (IV) with benzhydryl mercaptan by means of diethyl cyanophosphonate produced a mixture of cis (V) and trans (VI) phosphinothioic esters,which were separated by fractional crystallization from EtOAc.Finally,deprotection of both benzhydryl groups from the cis isomer (V) by means of trifluoroacetic acid yielded the title diacid.