(α-L-Rhamnopyranosyl)methylphosphonic acid and methyl (2-O-methyl-α-L-rhamnopyranosyl)methylphosphonate have been synthesized starting from allyl 3,4-di-O-benzyl-2-O-pmethoxybenzyl-α-L-rhamnopyranoside. The complete NMR spectroscopic characterization of these two compounds and the comparison of the theoretical and experimental vicinal coupling constants indicates a marked preference for the 1C4 conformation for both compounds, in analogy with the natural phosphate.
(alpha-L-rhamnopyranosyl)methylphosphonic acids : experimental evidence of the analogy with alpha-L-rhamnopyranosyl phosphate / S. Ronchi, F. Compostella, L. Lay, F. Ronchetti, L. Toma. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - 2005:20(2005 Oct), pp. 4459-4463. [10.1002/ejoc.200500440]
(alpha-L-rhamnopyranosyl)methylphosphonic acids : experimental evidence of the analogy with alpha-L-rhamnopyranosyl phosphate
S. RonchiPrimo
;F. Compostella
;L. Lay;F. RonchettiPenultimo
;
2005
Abstract
(α-L-Rhamnopyranosyl)methylphosphonic acid and methyl (2-O-methyl-α-L-rhamnopyranosyl)methylphosphonate have been synthesized starting from allyl 3,4-di-O-benzyl-2-O-pmethoxybenzyl-α-L-rhamnopyranoside. The complete NMR spectroscopic characterization of these two compounds and the comparison of the theoretical and experimental vicinal coupling constants indicates a marked preference for the 1C4 conformation for both compounds, in analogy with the natural phosphate.
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