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Titolo:
Efficient methods for the synthesis of [2-N-15]guanosine and 2 '-deoxy[2-N-15]guanosine derivatives
Autore:
Kamaike, K; Kinoshita, K; Niwa, K; Hirose, K; Suzuki, K; Ishido, Y;
Indirizzi:
Tokyo Univ Pharm & Life Sci, Sch Pharm, Lab Pharmaceut Chem, Tokyo 1920392, Japan Tokyo Univ Pharm & Life Sci Tokyo Japan 1920392 em, Tokyo 1920392, Japan Int Christian Univ, Coll Liberal Arts, Dept Chem, Div Nat Sci, Tokyo 1818585, Japan Int Christian Univ Tokyo Japan 1818585 Div Nat Sci, Tokyo 1818585, Japan
Titolo Testata:
NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS
fascicolo: 1-2, volume: 20, anno: 2001,
pagine: 59 - 75
SICI:
1525-7770(2001)20:1-2<59:EMFTSO>2.0.ZU;2-J
Fonte:
ISI
Lingua:
ENG
Soggetto:
ACID RELATED-COMPOUNDS; NITROGEN-15-LABELED DEOXYNUCLEOSIDES; PURINE NUCLEOSIDES; OLIGODEOXYNUCLEOTIDES; ADENOSINE;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Citazioni:
27
Recensione:
Indirizzi per estratti:
Indirizzo: Kamaike, K Tokyo Univ Pharm & Life Sci, Sch Pharm, Lab Pharmaceut Chem, 1432-1 Horinouchi, Tokyo 1920392, Japan Tokyo Univ Pharm & Life Sci 1432-1 Horinouchi Tokyo Japan 1920392
Citazione:
K. Kamaike et al., "Efficient methods for the synthesis of [2-N-15]guanosine and 2 '-deoxy[2-N-15]guanosine derivatives", NUCLEOS NUC, 20(1-2), 2001, pp. 59-75

Abstract

The nucleophlic addition-elimination reaction of 2',3',5'-tri-O-acety-2-fluoro-O-6- [2-(4-nitrophenyl)ethyl] inosine (8) with [N-15]benzylamine in the presence of triethylamine afforded the N-2-benzyl[2-N-15]guanosine derivative (13) in a high yield, which was further converted into the N-2-benzoyl[2-N-15] guanosine derivative by treatment with ruthenium trichloride and tetrabutylammonium periodate. A similar sequence of reactions of 2',3',5-tri-O-acety-2-fluoro-O-6- [2-(methylthio)ethyl]inosine (9) and the 6-chloro-2-fluoro-9-(beta -ribofuranosyl)-9H-purine derivative (11), which were respectively prepared from guanosine, with potassium [N-15]phthalimide afforded the N-2-phthaloyl [2-N-15]guanosine derivative (15; 62%) and 9-(2,3,5-tri-O-acetyl-beta -D-ribofuranosyl)-6-chloro-2- [N-15]phthalimido-9H-purine (17; 64%), respectively Compounds 15 and 17 were then efficiently converted into2',3',5'-tri-O-acetyl [2-N-15]guanosine. The corresponding 2'-deoxy derivatives (16 and 18) were also synthesized through similar procedures.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 12/07/20 alle ore 06:15:06