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SOME NOVEL NUCLEOSIDE REARRANGEMENTS EFFECTED BY (DIETHYLAMINO)SULPHUR TRIFLUORIDE - SYNTHESIS AND ANTIVIRAL PROPERTIES OF SOME FLUORINE-CONTAINING 3'-AZIDO-3'-DEOXYTHYMIDINE DERIVATIVES
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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 0022-1139.
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Abstract
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 | ||||
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Subjects: | Q Science > QD Chemistry | ||||
Journal or Publication Title: | JOURNAL OF FLUORINE CHEMISTRY | ||||
Publisher: | ELSEVIER SCIENCE SA LAUSANNE | ||||
ISSN: | 0022-1139 | ||||
Official Date: | June 1993 | ||||
Dates: |
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Volume: | 62 | ||||
Number: | 2-3 | ||||
Number of Pages: | 16 | ||||
Page Range: | pp. 145-160 | ||||
Publication Status: | Published |
Data sourced from Thomson Reuters' Web of Knowledge
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