7-SUBSTITUTED 7-DEAZA-2'-DEOXYGUANOSINES - REGIOSELECTIVE HALOGENATION OF PYRROLO[2,3-D]PYRIMIDINE NUCLEOSIDES

Autor(en): RAMZAEVA, N
SEELA, F
Stichwörter: ACID; CADEGUOMYCIN; Chemistry; Chemistry, Multidisciplinary; TRANSFER-RNA
Erscheinungsdatum: 1995
Herausgeber: NEUE SCHWEIZ CHEM GESELLSCHAFT
Journal: HELVETICA CHIMICA ACTA
Volumen: 78
Ausgabe: 5
Startseite: 1083
Seitenende: 1090
Zusammenfassung: 
The synthesis of 7-chloro-, 7-bromo-, and 7-iodo-substituted 7-deaza-2'-deoxyguanosine derivatives 2b-d is described. The regioselective 7-halogenation with N-halogenosuccinimides was accomplished using 7-[2-deoxy-3,5- O-di(2-methylpropanoyl)-beta-D-erytilro-pentofuranosyl]-2-(formylamino)- 4-methoxy-7H-pyrrolo[2,3-d]pyrimidine (4) as the common precursor. A one-pot reaction (2N aq. NaOH) of the halogenated intermediates 5a-c furnished the desired compounds. Also the 7-hexynyl derivative 2e of 7-deaza-2'-deoxyguanosine is described.
ISSN: 0018019X
DOI: 10.1002/hlca.19950780505

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