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首页> 外文期刊>current protocols in nucleic acid chemistry >Synthesis of 9-(6-Deoxy-α-L-Talofuranosyl)-6-Methylpurine and 9-(6-Deoxy-β-D-Allofuranosyl)-6-Methylpurine Nucleosides
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Synthesis of 9-(6-Deoxy-α-L-Talofuranosyl)-6-Methylpurine and 9-(6-Deoxy-β-D-Allofuranosyl)-6-Methylpurine Nucleosides

机译：Synthesis of 9-(6-Deoxy-α-L-Talofuranosyl)-6-Methylpurine and 9-(6-Deoxy-β-D-Allofuranosyl)-6-Methylpurine Nucleosides

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© 2020 John Wiley Sons, Inc.6-Methylpurine (MeP) is a cytotoxic adenine analog that does not exhibit selectivity when administered systemically and could be very useful in a gene therapy approach to cancer treatment involving Escherichia coli purine nucleoside phosphorylase (PNP). 9-(6-Deoxy-β-D-allofuranosyl)-6-methylpurine methyl(allo)-MePR, 18 and 9-(6-deoxy-α-L-talofuranosyl)-6-methylpurine methyl(talo)-MePR, 21 were synthesized as potential prodrugs for MeP in the E. coli PNP/prodrug cancer gene therapy approach. The detailed syntheses of methyl(allo)-MePR and methyl(talo)-MePR are described. The glycosyl donors, 1,2-di-O-acetyl-3,5-di-O-benzyl-α-D-allofuranose (12) and 1-O-acetyl-3-O-benzyl-2,5-di-O-benzoyl-α-L-talofuranose (16) were prepared from 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (4) in nine and eleven steps, respectively. Vorbrüggen coupling of the latter glycosyl donors with 6-methylpurine (3), followed by deprotection of the sugar hydroxyl groups, gave the title compounds in good overall yields. © 2020 by John Wiley Sons, Inc. Basic Protocol 1: Preparation of 6-methylpurine. Basic Protocol 2: Preparation of the D-allofuranose derivative (12). Basic Protocol 3: Preparation of 6-deoxy-α-L-talofuranoside. Basic Protocol 4: Preparation of methyl(allo)-MePR (18). Basic Protocol 5: Preparation of methyl(talo)-MePR (21).

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