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

Frank      Seela; Xiaohua      Peng

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

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Current Topics in Medicinal Chemistry

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

Volume: 6 Issue: 9

Author(s): Frank Seela and Xiaohua Peng

Affiliation:

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

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.

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Seela Frank and Peng Xiaohua, Progress in 7-Deazapurine - Pyrrolo[2,3-d]pyrimidine - Ribonucleoside Synthesis, Current Topics in Medicinal Chemistry 2006; 6 (9) . https://dx.doi.org/10.2174/156802606777303649

DOI https://dx.doi.org/10.2174/156802606777303649	Print ISSN 1568-0266
Publisher Name Bentham Science Publisher	Online ISSN 1873-4294

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