Current Topics in Medicinal Chemistry

Author(s): Frank Seela and Xiaohua Peng

DOI: 10.2174/156802606777303649

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Progress in 7-Deazapurine - Pyrrolo[2,3-d]pyrimidine - Ribonucleoside Synthesis

Page: [867 - 892] Pages: 26

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Abstract

This review reports on the synthesis of 7-deazapurine ribonucleosides, including C-nucleosides, 2-C-methyl derivatives and L-enantiomers. It covers the various aspects of convergent nucleoside synthesis such as the Schiff base procedure, the fusion reaction, the metal salt procedures, the Silyl-Hilbert-Johnson reaction, and the nucleobase anion glycosylation. The review discusses the scope and limitations of glycosylation reactions performed on 7-deazapurines. Peracylated ribose derivatives were now employed in the glycosylation, which overcome difficulties reported earlier.

Keywords: 7-deazapurine, pyrrolo[2,3-d]pyrimidine, ribonucleoside, glycosylation, C-nucleoside, L-nucleoside, natural occurrence, pharmacological properties