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

✍ Scribed by Jinggao Liu; Daniel H. O'Brien; Kurt J. Irgolic

Publisher
John Wiley and Sons
Year
1996
Tongue
English
Weight
796 KB
Volume
10
Category
Article
ISSN
0268-2605

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✦ Synopsis

Eight arsenic-containing ribosides were prepared from dimethyl( 1 -0-methyl1 -5-deoxy-2,3-0-isopropylidene-P-D-ribofuranos-5-yl)arsine and (2's)-

Reactions of the arsines with sulfur produced the compounds with a (CH,),As=S group as substituent in the 5-position. Treatment of these dimethyl(ribosy1)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(ribosy1)arsonium iodides. These arsonium iodides were reacted with trifluoroacetic acid/water. Anomeric mixtures of the deprotected compounds were isolated. Deprotection of the dimethyl(ribosy1)arsines proceeded without anomerization. Reaction of the dimethyl[ l-O-(2',3'-dihydroxypropyl)-5deoxy-P-~-ribofuranos-5-yl]arsine with methyl iodide produced the pure p-anomer of the arsonium iodide. The yields in these reactions were approximately 80%.

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