SYNTHESIS OF 6-SUBSTITUTED PURINE N-7-(2-DEOXY-BETA-D-RIBONUCLEOSIDES) VIA ANION GLYCOSYLATION AND ANOMERIZATION DURING THE N-7/N-9-GLYCOSYL TRANSFER

Autor(en): SEELA, F
WINTER, H
Stichwörter: 2'-DEOXYRIBONUCLEOSIDES; ACID RELATED-COMPOUNDS; ANALOGS; Biochemistry & Molecular Biology; CONVERSION; NOE DIFFERENCE SPECTROSCOPY; NUCLEOSIDES; OLIGODEOXYRIBONUCLEOTIDES; PHASE-TRANSFER GLYCOSYLATION; SODIUM-SALT GLYCOSYLATION; STABILITY
Erscheinungsdatum: 1995
Herausgeber: TAYLOR & FRANCIS INC
Journal: NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS
Volumen: 14
Ausgabe: 1-2
Startseite: 129
Seitenende: 142
Zusammenfassung: 
The synthesis of the 7-(2-deoxy-beta-D-erythro-pentofuranosyl) adenine (Ib) as well as the corresponding hypoxanthine- and purine nucleosides 3 and 4 is described employing the stereoselective nucleobase anion glycosylation. The N-7/N-9- isomer distribution of the 6-substituted purine (2-deoxyribonucleosides) depends on 6-substituent. Glycosyl transfer of 8a resulted in anomerization and yielded a mixture of the anomeric 6-methoxypurine N-9-(2-deoxy-D-ribonucleosides) 7a/7d. The preferred glycosylic bond conformation of purine N-7-(2-deoxyribonucleosides) is anti.
ISSN: 15257770
DOI: 10.1080/15257779508014658

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