| dc.date.accessioned |
2017-06-06T13:20:46Z |
und |
| dc.date.accessioned |
2017-10-24T12:19:33Z |
|
| dc.date.available |
2017-06-06T13:20:46Z |
und |
| dc.date.available |
2017-10-24T12:19:33Z |
|
| dc.date.issued |
2017-06-06T13:20:46Z |
|
| dc.identifier.uri |
http://radr.hulib.helsinki.fi/handle/10138.1/6065 |
und |
| dc.identifier.uri |
http://hdl.handle.net/10138.1/6065 |
|
| dc.title |
Synthesis of 6-aryl-2'-deoxyuridine derivatives |
en |
| ethesis.discipline |
Organic chemistry |
en |
| ethesis.discipline |
Orgaaninen kemia |
fi |
| ethesis.discipline |
Organisk kemi |
sv |
| ethesis.department.URI |
http://data.hulib.helsinki.fi/id/c2dd677c-da9c-4011-94b0-27b1585ac1cb |
|
| ethesis.department |
Kemiska institutionen |
sv |
| ethesis.department |
Department of Chemistry |
en |
| ethesis.department |
Kemian laitos |
fi |
| ethesis.faculty |
Matematisk-naturvetenskapliga fakulteten |
sv |
| ethesis.faculty |
Matemaattis-luonnontieteellinen tiedekunta |
fi |
| ethesis.faculty |
Faculty of Science |
en |
| ethesis.faculty.URI |
http://data.hulib.helsinki.fi/id/8d59209f-6614-4edd-9744-1ebdaf1d13ca |
|
| ethesis.university.URI |
http://data.hulib.helsinki.fi/id/50ae46d8-7ba9-4821-877c-c994c78b0d97 |
|
| ethesis.university |
Helsingfors universitet |
sv |
| ethesis.university |
University of Helsinki |
en |
| ethesis.university |
Helsingin yliopisto |
fi |
| dct.creator |
Jaidzeka, Rene Burinyuy |
|
| dct.issued |
2017 |
|
| dct.language.ISO639-2 |
eng |
|
| dct.abstract |
It is quite rare to find 6-substituted pyrimidines in nature due to the difficulty involved in directly introducing a substituent to the 6-position whereas other synthetic analogues of naturally occurring nucleosides like 5-substituted derivatives are more common.
The aim was to synthesize 3',5'-O,O-bis(tert-butyldimethylsilyl)-6-phenyl-2'-deoxyuridine by carrying out a direct nucleophilic substitution of 3',5'-O,O-bis(tert-butyldimethylsilyl)-6-cyano-2'-deoxyuridine with the Grignard reagent: phenyl magnesium bromide in the presence of zinc (II) chloride catalyst.
The first step was silylation of commercially available 2'-deoxyuridine and subsequent bromination at the 5-position to give 3',5'-O,O-bis(tert-butyldimethylsilyl)-5-bromo-2'-deoxyuridine. This was reacted with the nucleophile KCN to yield a product with the cyano substitute at the 6-position via intramolecular nucleophilic substitution. The final step was to introduce an aryl substituent to the 6-position to yield the target molecule. |
en |
| dct.language |
en |
|
| ethesis.language.URI |
http://data.hulib.helsinki.fi/id/languages/eng |
|
| ethesis.language |
English |
en |
| ethesis.language |
englanti |
fi |
| ethesis.language |
engelska |
sv |
| ethesis.thesistype |
pro gradu-avhandlingar |
sv |
| ethesis.thesistype |
pro gradu -tutkielmat |
fi |
| ethesis.thesistype |
master's thesis |
en |
| ethesis.thesistype.URI |
http://data.hulib.helsinki.fi/id/thesistypes/mastersthesis |
|
| dct.identifier.urn |
URN:NBN:fi-fe2017112251550 |
|
| dc.type.dcmitype |
Text |
|
