Synthesis of 1-O-(2?,3?-dihydroxypropyl)5-deoxy-?-D-ribofuranosides with (CH3)2As, (CH3)2As?S or (CH3)3As+ groups as substituents at the 5-position

Eight arsenic-containing ribosides were prepared from dimethyl(1-O-methyl1-5-deoxy-2,3-O-isopropylidene-β-D-ribofuranos-5-yl)arsine and (2′S)-dimethyl[1-O-(2′,3′-isopropylidenedioxypropyl)-5-deoxy-2,3-O-isopropylidene-β-D-ribofuranos-5-yl]arsine. Reactions of the arsines with sulfur produced the compounds with a (CH3)2As &&dbond S group as substituent in the 5-position. Treatment of these dimethyl(ribosyl)arsine sulfides with trifluoroacetic acid water removed the isopropylidene groups and gave the unprotected derivatives as thick oils in 80% yield. The arsines and methyl iodide gave the protected trimethyl(ribosyl)arsonium iodides. These arsonium iodides were reacted with trifluoroacetic acid/water. Anomeric mixtures of the deprotected compounds were isolated. Deprotection of the dimethyl(ribosyl)arsines proceeded without anomerization. Reaction of the dimethyl[1-O-(2′,3′-dihydroxypropyl)-5-deoxy-β-D-ribofuranos-5-yl]arsine with methyl iodide produced the pure β-anomer of the arsonium iodide. The yields in these reactions were approximately 80%.

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