Pyrrolo[2,3-d]pyrimidine β-L-Nucleosides Containing 7-Deazaadenine, 2-Amino-7-deazaadenine, 7-Deazaguanine, 7-Deazaisoguanine, and 7-Deazaxanthine

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Title:Pyrrolo[2,3-d]pyrimidine β-L-Nucleosides Containing 7-Deazaadenine, 2-Amino-7-deazaadenine, 7-Deazaguanine, 7-Deazaisoguanine, and 7-Deazaxanthine
Creators:
Seela, Frank
Peng, Xiaohua
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 71, 7, pp. 956-977
Uncontrolled Keywords:β-L-2'-Deoxyribonucleosides, CD spectroscopy, Nucleobase anion glycosylation, Pyrrolo[2,3-<i>d</i>]pyrimidines, Purines, Nucleosides, Antiviral activity, 7-Deazapurines, β-L-Ribonucleosides, NMR spectroscopy

Abstract

The synthesis and properties of 7-deazapurine β-L-nucleosides are described. The stereoselective glycosylation of the anions of 2-amino-6-chloro-7-deazapurines <strong>9a</strong>, <strong>9b</strong> or 6-chloro-7-deazapurines <strong>13a</strong>, <strong>13d</strong> with 3,5-di-<i>O</i>-(4-methylbenzoyl)-2-deoxy-α-L-<i>erythro</i>-pentofuranosyl chloride (<strong>8</strong>) furnished the β-L-2'-deoxyribonucleosides <strong>1</strong>-<strong>4</strong>. The synthesis of β-L-ribonucleosides <strong>5</strong>-<strong>7</strong> used the Silyl-Hilbert-Johnson reaction (TMSOTf/BSA/MeCN) performed under Vorbrüggen conditions for the glycosylation of 7-halogenated 6-chloro-2-pivalamido-7-deazapurines <strong>17b</strong>-<strong>17d</strong> with 1-<i>O</i>-acetyl-2,3,5-tri-<i>O</i>-benzoyl-L-ribofuranose (<strong>16</strong>). Single-crystal X-ray analyses were performed and CD spectra were measured to assign the configuration. The antiviral activity against selected DNA and RNA viruses is reported. <p>

Title:Pyrrolo[2,3-d]pyrimidine β-L-Nucleosides Containing 7-Deazaadenine, 2-Amino-7-deazaadenine, 7-Deazaguanine, 7-Deazaisoguanine, and 7-Deazaxanthine
Creators:
Seela, Frank
Peng, Xiaohua
Uncontrolled Keywords:β-L-2'-Deoxyribonucleosides, CD spectroscopy, Nucleobase anion glycosylation, Pyrrolo[2,3-<i>d</i>]pyrimidines, Purines, Nucleosides, Antiviral activity, 7-Deazapurines, β-L-Ribonucleosides, NMR spectroscopy
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:71
Number:7
Page Range:pp. 956-977
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20060956UNSPECIFIED
ID Code:2518
Item Type:Article
Deposited On:06 Feb 2009 17:19
Last Modified:06 Feb 2009 16:19

Citation

Seela, Frank; Peng, Xiaohua (2006) Pyrrolo[2,3-d]pyrimidine β-L-Nucleosides Containing 7-Deazaadenine, 2-Amino-7-deazaadenine, 7-Deazaguanine, 7-Deazaisoguanine, and 7-Deazaxanthine. Collection of Czechoslovak Chemical Communications, 71 (7). pp. 956-977. ISSN 0010-0765

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