FACILE SYNTHESIS OF 2'-DEOXYISOGUANOSINE AND RELATED 2',3'-DIDEOXYRIBONUCLEOSIDES

Autor(en): SEELA, F
GABLER, B
Stichwörter: 2',3'-DIDEOXYADENOSINE; ACID; AGENTS; ANALOGS; Chemistry; Chemistry, Multidisciplinary; GLYCOSYLATION; NUCLEOBASE ANION; NUCLEOSIDES
Erscheinungsdatum: 1994
Herausgeber: NEW SWISS CHEMICAL SOC
Journal: HELVETICA CHIMICA ACTA
Volumen: 77
Ausgabe: 3
Startseite: 622
Seitenende: 630
Zusammenfassung: 
The 2'-deoxyisoguanosine (1) was synthesized by a two-step procedure from 2'-deoxyguanosine (5). Amination of silylated 2'-deoxyguanosine yielded 2-amino-2'-deoxyadenosine (6) which was subjected to selective deamination of the 2-NH2 group resulting in compound 1. Also 2',3'-dideoxyisoguanosine (2) was prepared employing the photo-substitution of the 2-substituent of 2-chloro-2',3'-dideoxyadenosine (4). The latter was synthesized by Barton deoxygenation from 2-chloro-2'-deoxyadenosine (3) or via glycosylation of 2,6-dichloropurine (12) with the lactol 13. Compound 1 was less stable at the N-glycosylic bond than 2'-deoxyguanosine (5). The dideoxynucleoside 2 was deaminated by adenosine deaminase affording 2',3'-dideoxyxanthosine (17).
ISSN: 0018019X
DOI: 10.1002/hlca.19940770305

Show full item record

Page view(s)

2
Last Week
0
Last month
0
checked on Feb 24, 2024

Google ScholarTM

Check

Altmetric