Premium
Synthesis of 1‐ O ‐(2′,3′‐dihydroxypropyl)5‐deoxy‐β‐ D ‐ribofuranosides with (CH 3 ) 2 As, (CH 3 ) 2 AsS or (CH 3 ) 3 As + groups as substituents at the 5‐position
Author(s) -
Liu Jinggao,
O'Brien Daniel H.,
Irgolic Kurt J.
Publication year - 1996
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/(sici)1099-0739(199602)10:1<13::aid-aoc467>3.0.co;2-g
Subject(s) - chemistry , arsine , trifluoroacetic acid , substituent , iodide , yield (engineering) , methyl iodide , medicinal chemistry , bromide , organic chemistry , catalysis , phosphine , materials science , metallurgy
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 (CH 3 ) 2 As &&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%.