E. de Vroom

An approach towards the formation of an ester bond between the primary hydroxyl of a β-D-galactopyranoside and 2-aminoethylphosphonic acid and N-methyl substituted derivatives

Abstract An expeditious method for the preparation of the phosphonylating reagent 2-bromoethylphosphonic acid is presented. The latter compound as well as salicylchlorophosphite proved to be suitable for the synthesis of methyl 0-6-(2′-aminoethylphosphonyl)-β-D-galactopyranoside and N-mono- or dimethylated derivatives thereof.

Stereoselective Synthesis of Ribonucleoside 3′,5′-Cyclic Methyl(phenyl)phosphonates and Phosphonothioates

Abstract Monophosphonylation of 2′-protected ribonucleosides (i.e. 2′-O-THP-uridine and 2′-O-THP-N 6-levulinoyl-adenosine) with the bifunctional reagents bis[(6-trifluoromethyl)benzotriazol-1-yl] methyl(phenyl)phosphonates or the analogous phosphonothioates, and subsequent addition of N-methylimidazole, gave the chirally pure 3′,5′-cyclic methyl(phenyl)phosphonate or phosphonothioate derivatives, respectively. Deblocking of the fully protected compounds yielded, as evidenced by X-ray analysis, the corresponding pure Sp-diastereoisomers.