Use this URL to cite or link to this record in EThOS: | https://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.561554 |
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Title: | Synthesis of gemcitabine and it's tetrafluorinated analogues | ||||||
Author: | Brown, Kylie J. |
ISNI:
0000 0004 2727 3084
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Awarding Body: | University of Southampton | ||||||
Current Institution: | University of Southampton | ||||||
Date of Award: | 2011 | ||||||
Availability of Full Text: |
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Abstract: | |||||||
A novel synthesis of the 2-deoxy-2,2-difluorocytidine nucleoside analogue gemcitabine has been achieved. Starting from the known 3,5-O-dibenzoyl-2- deoxy-2,2-difluororibose, the nucleobase moiety is constructed in a linear fashion, using amino- or urea glycosylation methodology. This methodology has also been employed to synthesise nucleosides containing a tetrafluorinated ribose sugar and has been compared to conventional convergent nucleobase introduction methods. In this respect, a high-yielding Mitsunobu-based protocol has also been developed. Both purine and pyrimidine analogues have been synthesised. The aminoglycosylation methodology has been investigated with a range of amines. The methodology proves high-yielding for primary amines and lesshindered secondary amines. In contrast to expectations, their stability in acidic media was not very high. Anomerisation and ring isomerisation studies have been conducted.
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Supervisor: | Linclau, Bruno | Sponsor: | Not available | ||||
Qualification Name: | Thesis (Ph.D.) | Qualification Level: | Doctoral | ||||
EThOS ID: | uk.bl.ethos.561554 | DOI: | Not available | ||||
Keywords: | QD Chemistry | ||||||
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