Liebigs Annalen der Chemie

Stereoselective synthesis of 2??azapurine 2′??deoxy?螃漫?D??ribonucleosides by nucleobase??anion glycosylation

Z Kazimierczuk, F Seela

Index: Kazimierczuk, Zygmunt; Seela, Frank Liebigs Annalen der Chemie, 1990 , # 7 p. 647 - 651

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Citation Number: 5

Abstract

Abstract Nucleobase-anion glycosylation of 6-(methylthio)-2-azapurine (1) with 2-deoxy-3, 5- di-O-(p-toluoyl)-α-D-erythro-pentofuranosyl chloride (2) yields the 2′-deoxy-β-D- ribofuranosides 3–5 stereoselectively. The distribution of regioisomers is as follows: N-9 (32%); N-2 (30%), and N-7 (7%) together with a minor amount of an unidentified labile glycosylation product. The anomeric configuration and the site of glycosylation have been ...

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