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
Subjects:	Q Science > QD Chemistry
Journal or Publication Title:	JOURNAL OF FLUORINE CHEMISTRY
Publisher:	ELSEVIER SCIENCE SA LAUSANNE
ISSN:	0022-1139
Date:	June 1993
Volume:	62
Number:	2-3
Number of Pages:	16
Page Range:	pp. 145-160
Publication Status:	Published
URI:	http://wrap.warwick.ac.uk/id/eprint/21250

Data sourced from Thomson Reuters' Web of Knowledge

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