Pyrimidine Nucleosides. I. A New Route for the Synthesis of Thymine Nucleosides1
摘要：
A simplified method is given for the synthesis in good yields of thymine nucleosides by the condensation of a mercury derivative of thymine directly with poly-O-acylglycosyl halides followed by removal of protecting acetyl or benzoyl groups. Glycopyranosylthymines obtained by this "mercuri" procedure are shown to be identical with those obtained by the Hilert-Johnson method. The mercuri procedure is extremely useful for the preparation of pentofuranosyl nucleosides of thymine. The synthesis and characterization of 1-β-D-ribofuranosylthymine and 1-β-D-xylofuranosylthymine are reported and the former shown to be identical with an enzymically prepared material. 2,3,5-Tri-O-benzoylpentosyl halides are utilized for pentofuranosylthymine synthesis and their superiority to their corresponding tri-O-acetylpentofuranosyl halides is indicated. The synthesis of 1-O-acetyl-2,3,5-tri-O-benzoyl-α-D-xylose is reported.
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DOI：
10.1021/ja01591a024
被引量：
年份：
1956
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