City Research Online

Abstract

The use of nucleoside analogues as antiviral and carcinostatic agents is gaining widespread prominence in clinical practices. The introductory sections of this thesis describe their impor-tance. This study considers the attempted synthesis of one such analogue - 2' [2-amino,3(p-methoxypheny1)propanamido]-2/- deoxy-N6N6-dimethyladenosine, an isomer of the antibiotic Puromycin, which is a common clinically prescribed antibiotic. The two functional groups present (the sugar and base functions) make the nucleoside a somewhat difficult compound to work with. This is well reflected in the commercial cost of compounds of this type.

This study considers the synthesis of the common clinically used antiviral agent adenosine arabinoside (Ara-A) as the pre-cursor to the synthesis of the target compound. The approaches adopted have been firstly the direct manipulation of the sugar function and secondly the established method of transglycosy- lation. The former approach has been facilitated by the use of 1,3-dich1oro,1,1,3,3-tetraisopropy1disiloxane(TIPDS-CI2) as a highly selective protective group and the new reagent,dimethyl- aminopyridine (DMAP) as a specific hypernucleophi1ic agent. The synthetic route has been beset by other difficulties, one of which we think might be due to the electrostatic effect of this new protective group not previously investigated. The study considers these problems and the attempts at using different routes to the final synthesis.

Publication Type:	Thesis (Doctoral)
Subjects:	Q Science > QD Chemistry
Departments:	School of Science & Technology School of Science & Technology > School of Science & Technology Doctoral Theses Doctoral Theses

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