99709-52-1Relevant articles and documents
METHOD OF THE SYNTHESIS OF DIALKYL HALOALKYLPHOSPHONATES AND DIALKYL HALOALKYLOXYALKYLPHOSPHONATES
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Page/Page column 19-20, (2012/02/13)
The invention deals with the method of the synthesis of dialkyl haloalkylphosphonates and dialkyl haloalkyloxyalkylphosphonates via a microwave-heated Michaelis-Arbuzov reaction of trialkylphosphites with dihaloalkanes or bis(haloalkyl)ethers in a closed vessel, during which the reaction mixture, containing a dihaloalkane or bis(haloalkyl)ether and a trialkylphosphite, is heated with microwave radiation with the standard frequency (2.45 GHz) to reach a reaction temperature which is specific for each individual halogen. In the subsequent reaction of the first dihaloalkane or bis(haloalkyl)ether halogen atom with trialkyl phosphite, the desired dialkyl haloalkylphosphonate or dialkyl haloalkyloxyalkylphosphonate is formed, but the reaction of its halogen atom with the so-far present trialkylphosphite, leading to the creation of the relevant bisphosphonate, no longer takes place. In the case of an inhomogeneous reaction mixture, also the desired product in the amount of 0.1-5 molar % is added to the reaction mixture for its homogenization, which homogenizes it and thus precludes its uncontrollable overheating. The entire process of synthesis is more effective, faster, less expensive and more environmentally friendly than the methods described so far in the literature. The possibility of performing the described procedure also in a continuous-flow microwave reactor allows industrial production with minimal demands on an optimization of the reaction conditions for larger quantities, eliminates some security risks, dramatically reduces the spatial demands in production and reduces the need for the usage of large-tonnage industrial reactors.
Biosynthesis of Naturally Products with a P-C Bond. Part 6. Preparation of Deuterium- and Carbon-13-Labelled L-Alanyl- and L-Alanyl-L-alanyl-(2-aminoethyl)phosphonic Acids and their Use in Biosynthetic Studies of Fosfomycin in Streptomyces fradiae
Hammerschmidt, Friedrich,Kaehlig, Hanspeter,Mueller, Norbert
, p. 365 - 369 (2007/10/02)
(2-Aminoethyl)phosphonic acid (AEP) is not taken up by Streptomyces fradiae in the biosynthesis of fosfomycin.Attachment of L-alanine or L-alanyl-L-alanine to the amino group of deuteriated AEP affords di- and tri-peptides 4 and 5 which are transported into the cell. AEP is synthesized from Na(13)CN and the tosyloxymethylphosphonate 7.It is transformed into dipeptide 4d, which acts as a carrier for AEP which is incorporated into fosfomycin with an enrichment of 2 percent.
