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The Synthesis and Conformation of Dihydroxypiperidinyl Derivates of Nucleobases as Novel Iminosugar Nucleoside Analogs
Author(s) -
Rejman Dominik,
Pohl Radek,
Dračínský Martin
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201001610
Subject(s) - iminosugar , chemistry , nucleobase , glycosidic bond , stereochemistry , nucleoside , piperidine , chirality (physics) , nucleoside analogue , dna , organic chemistry , enzyme , biochemistry , nambu–jona lasinio model , chiral symmetry breaking , physics , quantum mechanics , quark
An optimized method for the synthesis of an important chiral scaffold, (3 S ,4 R ,5 R )‐1‐ N ‐Boc‐3,4‐isopropylidene‐3,4,5‐trihydroxypiperidine, 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.