SYNTHESIS AND PROPERTIES OF 3'-DEOXYPSICONUCLEOSIDES - ANOMERIC 1-(3-DEOXY-D-ERYTHRO-2-HEXULOFURANOSYL)THYMINES AND 9-(3-DEOXY-D-ERYTHRO-2-HEXULOFURANOSYL) ADENINES



: AZHAYEV A, GUZAEV A, HOVINEN J, MATTINEN J, SILLANPAA R, LONNBERG H

Publisher: GEORG THIEME VERLAG

: 1994

Synthesis: stuttgart

SYNTHESIS-STUTTGART

: SYNTHESIS-STUTTGART

: 4

: 396

: 400

: 5

: 0039-7881


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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