STEREOSELECTIVE SYNTHESIS OF INDAZOLE 2'-DEOXY-BETA-D-RIBONUCLEOSIDES - GLYCOSYLATION OF THE NUCLEOBASE ANION

Autor(en): SEELA, F
BOURGEOIS, W
Stichwörter: 2'-DEOXYRIBOFURANOSIDES; ADENINE DINUCLEOTIDES; Chemistry; Chemistry, Multidisciplinary; DERIVATIVES; DIFFERENCE; LIQUID; PHASE-TRANSFER GLYCOSYLATION; PYRAZOLO<3,4-D>PYRIMIDINES
Erscheinungsdatum: 1991
Herausgeber: NEW SWISS CHEMICAL SOC
Journal: HELVETICA CHIMICA ACTA
Volumen: 74
Ausgabe: 2
Startseite: 315
Seitenende: 322
Zusammenfassung: 
The glycosylation of indazolyl anions derived from 4a, b with 2-deoxy-3,5-bis-O-(4-methylbenzoyl)-alpha-D-erythro-pentofuranosyl chloride (5) is described. The reaction was stereoselective - exclusive beta-D-anomer formation - but regioisomeric N1-and N2-(2'-deoxy-beta-D-ribofuranosides) (i.e. 6a and 7a, resp., and 6b and 7b, resp.) were formed in about equal amounts. They were deprotected to yield 8a, b and 9a, b. Compound 1, related to 2'-deoxyadenosine (3), and its regioisomer 2 were obtained from 8b and 9b, respectively, by catalytic hydrogenation. The anomeric configuration as well as the position of glycosylation were determined by 1D NOE-difference spectroscopy. The first protonation site of 1 and 2 was found to be the NH2 group. The N-glycosylic bond of H-1-indazole N1-(2'-deoxyribofuranosides) is more stable than that of the parent purine nucleosides. Compound 1 is no substrate for adenosine deaminase.
ISSN: 0018019X
DOI: 10.1002/hlca.19910740209

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