Synthesis of carbohydrate mimetics by intramolecular 1,3-dipolar cycloaddition of N-(3-alkenyl)nitrones derived from unprotected D-aldopentoses

Wojciech Sas , Tomasz Rowicki , Maciej Malinowski , Monika Wielechowska , Patrycja Guzik

Abstract

Concise synthesis of C-furanosides has been achieved from unprotected D-xylose and D-arabinose. Reaction of both sugars with hydroxylamine 6 provided respective nitrones that underwent in situ intramolecular 1,3-dipolar cycloaddition yielding in each case a pair of diastereomeric derivatives of 7-oxa-1-azabicylo[2.2.1]heptane 7 and 8. The ratio of chromatographically separable diastereoisomers could be changed by carrying the reaction in the presence of weak Lewis acid. Both D-xylose-derived stereoisomers 7a and 8a were converted into D-erythro-Cfuranosides by tosylation or mesylation followed by catalytic hydrogenolysis. On the other hand the syntheses of Dthreofuranosides from D-arabinose derivatives 7b and 8b, carried out under similar conditions, were accompanied by the formation of minor amounts of polyhydroxyquinolizidines as a result of competitive N-alkylation. The polyhydroxyquinolizidine side-products have served for the assignment of absolute configuration of new compounds
Author Wojciech Sas (FC / DOC)
Wojciech Sas,,
- Department Of Organic Chemistry
, Tomasz Rowicki (FC / DOC)
Tomasz Rowicki,,
- Department Of Organic Chemistry
, Maciej Malinowski (FC / DOC)
Maciej Malinowski,,
- Department Of Organic Chemistry
, Monika Wielechowska (FC / IBC / DDTB)
Monika Wielechowska,,
- Department Of Drug Technology And Biotechnology
, Patrycja Guzik (FC / DOC)
Patrycja Guzik,,
- Department Of Organic Chemistry
Corporate authorThe Faculty of Chemistry, WUT (WCh)
Journal seriesEuropean Journal of Organic Chemistry, ISSN 1434-193X [1099-0690], (A 35 pkt)
Issue year2018
Vol2018
No6
Pages763-771
Publication size in sheets0.5
ASJC Classification1605 Organic Chemistry; 1606 Physical and Theoretical Chemistry
DOIDOI:10.1002/ejoc.201701512
URL http://onlinelibrary.wiley.com/doi/10.1002/ejoc.201701512/abstract
Languageen angielski
File
Rowicki 2018.pdf 1.82 MB
Score (nominal)35
ScoreMinisterial score = 35.0, 14-03-2019, ArticleFromJournal
Ministerial score (2013-2016) = 35.0, 14-03-2019, ArticleFromJournal
Publication indicators Scopus SNIP (Source Normalised Impact per Paper): 2016 = 0.653; WoS Impact Factor: 2017 = 2.882 (2) - 2017=2.675 (5)
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