In the presence of samarium iodide diethyl iodomethylphosphonate reacts with esters to afford beta-ketophosphonates. The protocol has been applied to sugar lactones to afford in fairly good yields intermediates that are useful precursors for a variety of potentially bioactive compounds, such as the C-glycosyl analogue of thymidine 5'-(beta-L-rhamnosyl)diphosphate.
SmI2-mediated reactions of diethyl iodomethylphosphonate with esters and lactones: a highly stereoselective synthesis of a precursor of the C-glycosyl analogue of thymidine 5′-(β-l-rhamnosyl)diphosphate / F. Orsini, A. Caselli. - In: TETRAHEDRON LETTERS. - ISSN 0040-4039. - 43:40(2002 Sep 30), pp. 7259-7261. [10.1016/S0040-4039(02)01540-X]
SmI2-mediated reactions of diethyl iodomethylphosphonate with esters and lactones: a highly stereoselective synthesis of a precursor of the C-glycosyl analogue of thymidine 5′-(β-l-rhamnosyl)diphosphate
F. OrsiniPrimo
;A. CaselliUltimo
2002
Abstract
In the presence of samarium iodide diethyl iodomethylphosphonate reacts with esters to afford beta-ketophosphonates. The protocol has been applied to sugar lactones to afford in fairly good yields intermediates that are useful precursors for a variety of potentially bioactive compounds, such as the C-glycosyl analogue of thymidine 5'-(beta-L-rhamnosyl)diphosphate.File | Dimensione | Formato | |
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