Synthesis of 9-(3-deoxy-3-C-methyl-β-d

Add time:08/03/2019    Source:sciencedirect.com

Reaction of methyl 2,3-anhydro-5-O-trityl-β-d-ribofuranoside (4) with methyl-magnesium chloride gave a mixture of methyl 3-chloro-3-deoxy-5-O-trityl-β-d-xylofuranoside (5) and methyl 3-deoxy-3-C-methyl-5-O-trityl-α-d-xylofuranoside (6). Removal of the trityl group from 6 gave methyl 3-deoxy-3-C-methyl-β-d-xylofuranoside (9), which, on treatment with p-nitrobenzoyl chloride, gave methyl 3-deoxy-3-C-methyl-2,5-di-O-(p-nitrobenzoyl)-β-d -xylofuranoside (10). The glycosyl chloride (15) derived from 10 reacted with 6-(benzamido)chloromercuripurine to give 6-(benzamido)-9-[3-deoxy-3-C-methyl-2,5-di-O-(p-nitrobenzoyl)-d-xylofuranosyl]purine (16). Alkaline methanolysis of 16 produced 9-(3-deoxy-3-C-methyl-α-d-xylofuranosyl)-adenine (α-1) and 9-(3-deoxy-3-C-methyl-β-d-xylofuranosyl)adenine (β-1) in the ratio of 1:4. Treatment of 6 with benzoyl chloride gave methyl 2-O-benzoyl-3-deoxy-3-C-methyl-5-O-trityl-β-d-xylofuranoside (17). The trityl group was removed from 17 to give methyl 2-O-benzoyl-3-deoxy-3-C-methyl-β-d-xylofuranoside (18), which was converted into methyl 2,5-di-O-benzoyl-3-deoxy-3-C-methyl-β-d-xylofuranoside (19). When the glycosyl halide (20) obtained from 19 reacted with 6-(benzamido)chloromercuripurine, 6-(benzamido)-9-(2,5-di-O-benzoyl-3-deoxy-3-C-methyl-d-xylofuranosyl)-purine (21) was produced. Ammonolysis of 21 gave α-1 and β-1 in the ratio of 1:16.

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