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Title:Uporaba alilnega intermediata pri novi sintezni poti do heterocikličnega gradnika rosuvastatina : N-(4-(4-fluorofenil)-5-formil-6-izopropilpirimidin-2-il)-N-metilmetansulfonamida
Authors:ID Čusak, Alen (Author)
ID Časar, Zdenko (Author)
ID Šterk, Damjan (Author)
Files:URL https://journals.um.si/index.php/anali-pazu/article/view/1986
 
.pdf Uporaba_alilnega_intermediata-Cusak-2017.pdf (1,10 MB)
MD5: 52EACF027B764FEC8FA51AD9A207FAB2
 
Language:Slovenian
Work type:Scientific work
Typology:1.01 - Original Scientific Article
Organization:UZUM - University of Maribor Press
Abstract:Z novo sintezno metodo smo pripravili N-(4-(4-fluorofenil)-5-formil-6-izopropilpirimidin-2-il)-N-metilmetansulfonamid, ki predstavlja ključni heterociklični gradnik rosuvastatina. Sinteza temelji na uvedbi alilne skupine na mesto 5 predhodno pripravljenega pirimidinskega derivata. Alilno substituiran pirimidinski intermediat je mogoče pretvoriti v N-(4-(4-fluorofenil)-5-formil-6-izopropilpirimidin-2-il)-N-metilmetansulfonamid v treh stopnjah, ki vključujejo izomerizacijo dvojne vezi, oksidacijo nastalega alkena v diol in oksidativno cepitev vicinalnega diola. Celotna štiristopenjska sinteza omogoča pripravo naslovne spojine s 60-odstotnim celokupnim izkoristkom, kar da odličen 88-odstotni povprečni izkoristek na stopnjo ob uporabi industrijsko sprejemljivih reagentov in blagih reakcijskih pogojev.
Keywords:statini, rosuvastatin, heterociklične spojine, pirimidini
Publication status:Published
Publication version:Version of Record
Publication date:01.01.2017
Place of publishing:Maribor
Publisher:Univerza v Mariboru, Univerzitetna založba
Year of publishing:2017
Number of pages:6
Numbering:Letn.7, št.1/2
PID:20.500.12556/DKUM-97313 New window
UDC:615:54
ISSN on article:2820-364X
COBISS.SI-ID:1359710 New window
DOI:10.18690/analipazu.7.1-2.18-23.2017 New window
Publication date in DKUM:27.02.2026
Views:140
Downloads:3
Metadata:XML DC-XML DC-RDF
Categories:Misc.
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Record is a part of a journal

Title:Anali PAZU
Publisher:Združenje Pomurska akademsko znanstvena unija, Združenje Pomurska akademsko znanstvena unija, Univerzitetna založba Univerze v Mariboru
ISSN:2232-416X
COBISS.SI-ID:257553152 New window

Licences

License:CC BY-NC-ND 4.0, Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International
Link:http://creativecommons.org/licenses/by-nc-nd/4.0/
Description:The most restrictive Creative Commons license. This only allows people to download and share the work for no commercial gain and for no other purposes.

Secondary language

Language:English
Title:Use of Allyl Intermediate in Novel Synthetic Route to Rosuvastatin Key Heterocyclic Building Block : N-(4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide
Abstract:A key building block of rosuvastatin was prepared via a novel synthetic method. Key feature of the presented synthetic approach is introduction of an allyl group into pyrimidine core at position 5. 5-Allyl substituted pyrimidine derivative can be transformed into title compound in three steps involving izomerisation of the allyl into alkene moiety, oxidation of the alkene moiety to the diol structure and oxidative cleavage of vicinal diol. Synthesis enables preparation of title compound in overall 60 % yield, which represents 88 % average yield per step by applying industrially acceptable reagents and mild conditions.
Keywords:statins, rosuvastatin, heterocycles, pyrimidines


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  1. Anali PAZU

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