(α‐ L ‐Rhamnopyranosyl)methylphosphonic Acids: Experimental Evidence of the Analogy with α‐ L ‐Rhamnopyranosyl Phosphate | Zendy

Ronchi Silvia | Zendy; Compostella Federica | Zendy; Lay Luigi | Zendy; Ronchetti Fiamma | Zendy; Toma Lucio | Zendy

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(α‐ L ‐Rhamnopyranosyl)methylphosphonic Acids: Experimental Evidence of the Analogy with α‐ L ‐Rhamnopyranosyl Phosphate

Author(s) -

Ronchi Silvia,

Compostella Federica,

Lay Luigi,

Ronchetti Fiamma,

Toma Lucio

Publication year - 2005

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.200500440

Subject(s) - chemistry , vicinal , stereochemistry , phosphate , natural compound , organic chemistry , engineering , biochemical engineering

(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 ‐ p ‐methoxybenzyl‐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 1 C 4 conformation for both compounds, in analogy with the natural phosphate. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

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