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The Synthesis and Conformation of Dihydroxypiperidinyl Derivates of Nucleobases as Novel Iminosugar Nucleoside Analogs
- 1.0359047 - ÚOCHB 2012 RIV DE eng J - Journal Article
Rejman, Dominik - Pohl, Radek - Dračínský, Martin
The Synthesis and Conformation of Dihydroxypiperidinyl Derivates of Nucleobases as Novel Iminosugar Nucleoside Analogs.
European Journal of Organic Chemistry. -, č. 11 (2011), s. 2172-2187. ISSN 1434-193X. E-ISSN 1099-0690
R&D Projects: GA MŠMT(CZ) LC06077; GA MŠMT 2B06065; GA AV ČR KJB400550903
Institutional research plan: CEZ:AV0Z40550506
Keywords : iminosugars * azanucleosides * nucleosides
Subject RIV: CC - Organic Chemistry
Impact factor: 3.329, year: 2011
An optimized method for the synthesis of an important chiral scaffold, was developed. Using this intermediate, the preparation of various chiral aminodihydroxypiperidines and their transformation into a series of non-glycosidic, six-membered azanucleosides was accomplished. NMR conformation analysis of the prepared piperidine azanucleosides revealed a preference for the chair conformation, with the nucleobase fixed in the equatorial position in all cases.
Permanent Link: http://hdl.handle.net/11104/0196920
Number of the records: 1