| Abstract: | The phosphonylation by oxirane/phosphorous acid is characterized by formation of spirophosphorane, which provides the active intermediate in the reaction, β-hydroxyalkyl alkylene phosphite. Here, we demonstrate that a well-known and readily accessible spirophosphorane, 2λ5-2,2′spirobi[1,3,2-benzodioxaphosphole] can be used as convenient and effective phosphonylating agent in similar reaction. The easily detectable primary 3-phenylpropyl H-phosphonate, as well as 5′-O-tritylthymidyl, 4-N-benzoyl-5′-O-trityl-deoxycytidyl, 5′-O-trityl-deoxycytidyl, 6-N-benzoyl-5′-O-trityl- deoxyadenosyl 5′-O-trityluridyl, and 2′,3′-isopropylidene-uridyl H-phosphonates were prepared using a simple and straightforward procedure. Our results provide an interesting example of the potential and the limitations of a synthetic approach utilising reaction of leaving of diol system. |
