SOME NOVEL NUCLEOSIDE REARRANGEMENTS EFFECTED BY (DIETHYLAMINO)SULPHUR TRIFLUORIDE - SYNTHESIS AND ANTIVIRAL PROPERTIES OF SOME FLUORINE-CONTAINING 3'-AZIDO-3'-DEOXYTHYMIDINE DERIVATIVES
UNSPECIFIED (1993) SOME NOVEL NUCLEOSIDE REARRANGEMENTS EFFECTED BY (DIETHYLAMINO)SULPHUR TRIFLUORIDE - SYNTHESIS AND ANTIVIRAL PROPERTIES OF SOME FLUORINE-CONTAINING 3'-AZIDO-3'-DEOXYTHYMIDINE DERIVATIVES. JOURNAL OF FLUORINE CHEMISTRY, 62 (2-3). pp. 145-160. ISSN 0022-1139Full text not available from this repository.
The reaction of pyrimidine nucleoside 5'-aldehydes with (diethylamino)sulphur trifluoride (DAST) to produce 5'-deoxy-5',5'-difluoronucleosides is reported. The preferred reaction is the production of the O2,5'-anhydro-5'-fluoronucleoside. If this is prevented by substitution at O4 or N-3 then, in the former case, either DAST no longer reacts or under drastic conditions the C(1')-N(1) bond breaks and the heterocyclic base remains joined by C-5' --> O2 to a glycosyl fluoride. In the latter case, the 5'-aldehyde of 2',3'-O-isopropylideneuridine gives the 5'-deoxy-5',5'-difluoro compound as the sole identifiable product. With the 5'-aldehyde of AZT [suitably protected at N-31 as starting material, treatment with DAST yields a diastereoisomeric mixture of glycosyl fluorides and a derivative of 5'-deoxy-5',5'-difluoro AZT from which 3'-azido-3',5'-dideoxy-5',5'-difluorothymidine could be isolated. This compound is not toxic nor has it any activity against human immunodeficiency virus type-1 (HIV-1) at concentrations up to 100 muM.
|Item Type:||Journal Article|
|Subjects:||Q Science > QD Chemistry|
|Journal or Publication Title:||JOURNAL OF FLUORINE CHEMISTRY|
|Publisher:||ELSEVIER SCIENCE SA LAUSANNE|
|Number of Pages:||16|
|Page Range:||pp. 145-160|
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