A1 Refereed original research article in a scientific journal
SYNTHESIS AND PROPERTIES OF 3'-DEOXYPSICONUCLEOSIDES - ANOMERIC 1-(3-DEOXY-D-ERYTHRO-2-HEXULOFURANOSYL)THYMINES AND 9-(3-DEOXY-D-ERYTHRO-2-HEXULOFURANOSYL) ADENINES
Authors: AZHAYEV A, GUZAEV A, HOVINEN J, MATTINEN J, SILLANPAA R, LONNBERG H
Publisher: GEORG THIEME VERLAG
Publication year: 1994
Journal:: Synthesis: stuttgart
Journal name in source: SYNTHESIS-STUTTGART
Journal acronym: SYNTHESIS-STUTTGART
Issue: 4
First page : 396
Last page: 400
Number of pages: 5
ISSN: 0039-7881
Abstract
Anomeric 1-(3-deoxy-D-erythro-2-hexulofuranosyl)thymines and 9-(3-deoxy-D-erythro-2-hexulofuranosyl)adenines were prepared by tin(IV) chloride catalyzed N-glycosylation of trimethylsilylated thymine and N-6-benzoyladenine with methyl 3-deoxy-D-erythro-2-hexulofuranoside triacetate or tribenzoate, respectively. These O-glycosides used as starting materials were obtained by deoxygenation of 1,2: 4,5-di-O-isopropylidene-beta-D-fructopyranose and subsequent acid-catalyzed methanolysis of the resulting 3-deoxy derivative. The anomeric configuration of the nucleosides prepared was assigned by a combination of X-ray crystallography and 2D H-1 NMR spectroscopy. The conformation and hydrolytic stability of these new nucleoside analogous are discussed.
Anomeric 1-(3-deoxy-D-erythro-2-hexulofuranosyl)thymines and 9-(3-deoxy-D-erythro-2-hexulofuranosyl)adenines were prepared by tin(IV) chloride catalyzed N-glycosylation of trimethylsilylated thymine and N-6-benzoyladenine with methyl 3-deoxy-D-erythro-2-hexulofuranoside triacetate or tribenzoate, respectively. These O-glycosides used as starting materials were obtained by deoxygenation of 1,2: 4,5-di-O-isopropylidene-beta-D-fructopyranose and subsequent acid-catalyzed methanolysis of the resulting 3-deoxy derivative. The anomeric configuration of the nucleosides prepared was assigned by a combination of X-ray crystallography and 2D H-1 NMR spectroscopy. The conformation and hydrolytic stability of these new nucleoside analogous are discussed.
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