Synthesis of Cyclic α-Amino Acids. IV. Syntheses of Adenine Nucleosides of 3-Amino-3-C-carboxy-3-deoxy-d-ribofuranose and 3-Amino-3-C-carboxy-3-deoxy-d-ribopyranose

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Abstract
9-(3′-Amino-3′-C-carboxy-3′-deoxy-β-d-ribofuranosyl)adenine (I) and 9-(3′-amino-3′-C-carboxy-3′-deoxy-β-d-ribopyranosyl)adenine (II) have been synthesized. They are the first examples of nucleoside-derivatives which have an α-amino acid structure in their furanose or pyranose ring. A masked derivative (VII) of α-d-erythro-pentofuranos-3-ulose was converted into a hydantoin derivative (IX), which was acetolyzed and then treated with dry hydrogen chloride to give an acylglycosyl chloride (XI). Condensation of this derivative with chloromercuri-6-benzamidopurine followed by hydrolysis afforded I. Treatment of the hydantoin derivative (IX) with methanolic hydrogen chloride followed by hydrolysis gave methyl 3-amino-3-C-carboxy-3-deoxy-α-d-ribopyranoside (XVII), which has been found to be identical with one of the isomers of methyl 3-amino-3-C-carboxy-3-deoxy-α-d-pentopyranoside previously reported. The 1-O-acetyl-3-N-benzoyl-2,4-di-O-benzoyl derivative of ethyl ester of this acid (XVII) was fused with 6-benzamidopurine in the presence of p-toluenesulfonic acid and followed by hydrolysis to afford II. Structural proofs for the new nucleoside-derivatives were obtained from their ultraviolet, infrared and nuclear magnetic resonance spectra.