Abstract
Abstract2‐Amino‐9‐β‐D‐ribofuranosylpurine‐2‐sulfonamide (2‐sulfamoyladenosine, 4), a congener of sulfonosine (3), was synthesized by four different routes. Acid catalyzed fusion of 6‐chloropurine‐2‐sulfonyl fluoride (5) with 1,2,3,5‐tetra‐O‐acetyl‐β‐D‐ribofuranose (8) gave a good yield of 6‐chloro‐9‐(2,3,5‐tri‐O‐acetyl‐β‐D‐ribofuranosyl)purine‐2‐sulfonyl fluoride (9). Ammonolysis of 9 furnished 4. Lewis acid catalyzed glycosylation of the trimethylsilyl derivative of either 6‐chloropurine‐2‐sulfonamide (6) or 6‐aminopurine‐2‐sulfonamide (7) with 8 gave the corresponding N9‐glycosylated products, 10 and 11, respectively, which on ammonolysis gave 4. Amination of 2‐thioadenosine (12) with chloramine solution gave the sulfenamide derivative 13, which on subsequent oxidation with m‐chloroperoxybenzoic acid furnished an alternate route to 4. The structure of 4 was established by single‐crystal X‐ray diffraction studies. 2‐Sulfamoyladenosine (4) is devoid of significant inhibitory activity against L1210 leukemia in mice.
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