Novel 2′-Deoxy Pyrazine C-Nucleosides Synthesized VIA Palladium-Catalyzed Cross-Couplings
The palladium-catalyzed cross-couplings of 2-chloro-3,5-diamino-6-iodopyrazine (1a) and methyl 3-amino-6-iodopyrazine-2-carboxylate (1b) with 1,4-anhydro-3,5-O-bis[(tert-butyl)dimethylsilyl]-2-deoxy-D-erythro-pent-1-enitol (2) followed by desilylation and stereospecific reduction of the 2′-deoxy-3′-...
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| Published in | Nucleosides & nucleotides Vol. 16; no. 10-11; pp. 1999 - 2012 |
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| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
| Published |
NEW YORK
Taylor & Francis Group
01.10.1997
Marcel Dekker Inc |
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| Abstract | The palladium-catalyzed cross-couplings of 2-chloro-3,5-diamino-6-iodopyrazine (1a) and methyl 3-amino-6-iodopyrazine-2-carboxylate (1b) with 1,4-anhydro-3,5-O-bis[(tert-butyl)dimethylsilyl]-2-deoxy-D-erythro-pent-1-enitol (2) followed by desilylation and stereospecific reduction of the 2′-deoxy-3′-keto adduct leads to the formation of 2-chloro-6-(2-deoxy-ß-D-ribofuranosyl)-3,5-diaminopyrazine (4a) and methyl 3-amino-6-(2-deoxy-ß-D-ribofuranosyl)pyrazine-2-carboxylate (4b) in 58% yield and 21% yield, respectively. These are the first syntheses of the heretofore unknown 2′-deoxy pyrazine C-nucleosides and demonstrate the utility of a convergent approach for the synthesis of pyrazine C-nucleosides. |
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| AbstractList | The palladium-catalyzed cross-couplings of 2-chloro-3,5-diamino-6-iodopyrazine (1a) and methyl 3-amino-6-iodopyrazine-2-carboxylate (1b) with 1,4-anhydro-3,5-O-bis[(tert-butyl)dimethylsilyl]-2-deoxy-D-erythro-pent-1-enitol (2) followed by desilylation and stereospecific reduction of the 2′-deoxy-3′-keto adduct leads to the formation of 2-chloro-6-(2-deoxy-ß-D-ribofuranosyl)-3,5-diaminopyrazine (4a) and methyl 3-amino-6-(2-deoxy-ß-D-ribofuranosyl)pyrazine-2-carboxylate (4b) in 58% yield and 21% yield, respectively. These are the first syntheses of the heretofore unknown 2′-deoxy pyrazine C-nucleosides and demonstrate the utility of a convergent approach for the synthesis of pyrazine C-nucleosides. The palladium-catalyzed cross-couplings of 2-chloro-3,5-diamino-6-iodopyrazine (1a) and methyl 3-amino-6-iodopyrazine-2-carboxylate (1b) with 1,4-anhydro-3,5-O-bis[(tert-butyl)dimethylsilyl] 2-deoxy-D-erythro-pent-1-enitol (2) followed by desilylation and stereospecific reduction of the 2'-deoxy-3'-keto adduct leads to the formation of 2-chloro-6-(2-deoxy-beta-D-ribofuranosyl)-3,5-diaminopyrazine (4a) and methyl 3-amino-6-(2-deoxy-beta-D-ribofuranosyl)pyrazine-2-carboxylate (4b) in 58% yield and 21% yield, respectively. These are the first syntheses of the heretofore unknown 2'-deoxy pyrazine C-nucleosides and demonstrate the utility of a convergent approach for the synthesis of pyrazine C-nucleosides. |
| Author | Wise, Dean S. Walker, John A. Hinkley, Jack M. Chen, Jiong J. Townsend, Leroy B. |
| Author_xml | – sequence: 1 givenname: John A. surname: Walker fullname: Walker, John A. organization: Department of Medicinal Chemistry, College of Pharmacy; Department of Chemistry , College of Literature, Science, and Arts, The University of Michigan – sequence: 2 givenname: Jiong J. surname: Chen fullname: Chen, Jiong J. organization: Department of Medicinal Chemistry, College of Pharmacy; Department of Chemistry , College of Literature, Science, and Arts, The University of Michigan – sequence: 3 givenname: Jack M. surname: Hinkley fullname: Hinkley, Jack M. organization: Department of Medicinal Chemistry, College of Pharmacy; Department of Chemistry , College of Literature, Science, and Arts, The University of Michigan – sequence: 4 givenname: Dean S. surname: Wise fullname: Wise, Dean S. organization: Department of Medicinal Chemistry, College of Pharmacy; Department of Chemistry , College of Literature, Science, and Arts, The University of Michigan – sequence: 5 givenname: Leroy B. surname: Townsend fullname: Townsend, Leroy B. organization: Department of Medicinal Chemistry, College of Pharmacy; Department of Chemistry , College of Literature, Science, and Arts, The University of Michigan |
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| CitedBy_id | crossref_primary_10_1016_S0008_6215_01_00256_7 crossref_primary_10_1002_hlca_200490120 crossref_primary_10_1021_op060107s crossref_primary_10_1021_ol052866l crossref_primary_10_1351_PAC_CON_12_11_10 crossref_primary_10_1016_j_tet_2010_02_026 crossref_primary_10_1021_jo000510b crossref_primary_10_1081_NCN_100105246 crossref_primary_10_1021_jm020299r crossref_primary_10_1002_chin_199815240 crossref_primary_10_1081_NCN_120006528 |
| Cites_doi | 10.1021/jo951376b 10.1021/jo00266a049 10.1021/jo00121a071 10.1021/om00102a002 10.1016/S0079-6468(08)70228-5 10.1021/jo00408a041 10.1002/hlca.19960790710 10.1021/ar00174a006 10.1016/0040-4039(96)01121-5 10.1021/jm00329a017 10.1021/ja00124a020 10.1080/07328309008543860 10.1007/978-1-4615-2824-1 10.1021/jo00043a029 10.1016/0022-328X(91)86074-Z 10.1021/jo01289a012 10.1080/00397919608003656 10.1080/07328318908054200 10.1016/0040-4039(95)01826-4 10.1080/15257779508014656 10.1039/c39840001287 10.1002/jhet.5570180838 10.1007/978-1-4757-9667-4 10.1021/om00029a005 10.1007/978-1-4613-0995-6 10.1080/07328318408079416 10.1002/jhet.5570310627 10.1021/jo00270a011 10.1021/jo00409a001 10.1039/jr9520000993 |
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| Keywords | REARRANGEMENT HALIDES ANOMERIC CONFIGURATION METALATION SPECTROSCOPY VINYLATION DIAZINES GLYCALS EFFICIENT |
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B. – ident: CIT0013 doi: 10.1080/00397919608003656 – ident: CIT0027 doi: 10.1080/07328318908054200 – ident: CIT0004b doi: 10.1016/0040-4039(95)01826-4 – volume-title: Comprehensive Heterocyclic Chemistry year: 1984 ident: CIT0014 contributor: fullname: Porter A. E. A. – ident: CIT0016 doi: 10.1080/15257779508014656 – ident: CIT0021 doi: 10.1039/c39840001287 – ident: CIT0026 doi: 10.1002/jhet.5570180838 – volume: 3 volume-title: Chemistry of Nucleosides and Nucleotides year: 1994 ident: CIT0001e doi: 10.1007/978-1-4757-9667-4 contributor: fullname: Townsend L. B. – ident: CIT0023 doi: 10.1021/om00029a005 – volume: 1 volume-title: Chemistry of Nucleosides and Nucleotides year: 1988 ident: CIT0001b doi: 10.1007/978-1-4613-0995-6 contributor: fullname: Townsend L. B. – ident: CIT0025 doi: 10.1080/07328318408079416 – ident: CIT0009 doi: 10.1002/jhet.5570310627 – ident: CIT0022 doi: 10.1021/jo00270a011 – ident: CIT0019 doi: 10.1021/jo00409a001 – ident: CIT0015 doi: 10.1039/jr9520000993 |
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| Snippet | The palladium-catalyzed cross-couplings of 2-chloro-3,5-diamino-6-iodopyrazine (1a) and methyl 3-amino-6-iodopyrazine-2-carboxylate (1b) with... |
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| StartPage | 1999 |
| SubjectTerms | Biochemistry & Molecular Biology Life Sciences & Biomedicine Science & Technology |
| Title | Novel 2′-Deoxy Pyrazine C-Nucleosides Synthesized VIA Palladium-Catalyzed Cross-Couplings |
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