707-61-9Relevant articles and documents
Synthesis of novel deoxy λ5 phospha sugar nucleosides: 1,3-dipolar cycloaddition of an azidophospholane with alkynes
Yamashita, Mitsuji,Mallikarjuna Reddy, Putta,Kato, Yukihiro,Krishna Reddy, Valluru,Suzuki, Kazumitsu,Oshikawa, Tatsuo
, p. 257 - 270 (2001)
Several novel phospha sugar nucleosides, analogs of normal sugar nucleosides, were synthesized from a phospholene 1-oxide derivative. Bromination of a phospholene precursor in aqueous organic medium gave regio diastereomers, the threo and erythro bromohydrins 3 (1-bromo-1,3,4-trideoxy-1,4-C-[(R,S)-phenylphosphinylidene]-glycero- tetrofuranose). Further substitution of the threo isomer 3a with sodium azide led to its corresponding azidophospholane 4 (1-azido-1,3,4-trideoxy-2-methyl-1,4-C-[(R)-phenylphosphinylidene]-β-D- glycero-tetrofuranose). 1,3-Dipolar cycloaddition of 4 with various electron-deficient and electron-rich alkynes afforded triazole derivatives that are nucleoside analogues. The strong electron-withdrawing phosphoryl group in the hemiacetal ring exerted no effect over reaction regioselectivity of the 1,3-dipolar cycloaddition, but steric effects of the alkynes played a vital role on the selectivity, since the regioisomer ratios and the rates and yields of cycloadducts changed as the bulkiness of the substituents on the acetylene changes. Structures of all compounds were unequivocally confirmed by 1H, 13C, and 31P NMR and mass spectral studies. Single crystal X-ray crystallographic analysis of some derivatives allowed determination of configuration of the phospha sugar nucleosides.
Isomerization and application of phospholene oxides
Herbay, Réka,Péczka, Nikolett,Gy?rke, Gábor,Bagi, Péter,Fogassy, Elemér,Keglevich, Gy?rgy
, p. 610 - 613 (2019/01/05)
In this research, an investigation of the isomerization and the applications of 3-phospholene oxides were elaborated. The isomerization of 3-phospholene oxides to 2-phospholene oxides was investigated under thermal condition. The application of bases and acids was also tested in this reaction. Moreover, the isomerization was also elaborated via the formation of halophosphonium salt intermediates. The 3-phospholene oxides were deoxygenated and transformed to the corresponding palladium complexes.
A novel preparation of chlorophospholenium chlorides and their application in the synthesis of phospholene boranes
Herbay, Réka,Bagi, Péter,Mucsi, Zoltán,Mátrav?lgyi, Béla,Drahos, László,Fogassy, Elemér,Keglevich, Gy?rgy
, p. 458 - 461 (2017/01/11)
A novel preparation of 1-chloro-3-methyl-3-phospholenium chlorides was developed by reacting 1-substituted-3-methyl-3-phospholene 1-oxides with oxalyl chloride. The obtained cyclic chlorophosphonium salts were reacted with LiBH4to afford the corresponding 1-substituted-3-methyl-3-phospholene boranes. The latter protocol involves a silane-free deoxygenation, and borane complex formation. In one instance, a 2-phospholene borane and the corresponding P-oxide were synthesized via rearrangement of the double bond in the cyclic chlorophosphonium salt. This double bond migration was investigated by quantum chemical calculations.