2'-Deoxy-3,7-dideazanebularine and 2'-Deoxy-3,7-dideazainosine: Synthesis of Pyrrolo[3,2-c]pyridine b-D-2'-Deoxyribofuranosides by Solid-liquid Phase-transfer Glycosylation
- 1 January 1987
- journal article
- research article
- Published by CLOCKSS Archive in HETEROCYCLES
- Vol. 26 (7) , 1755-1760
- https://doi.org/10.3987/r-1987-07-1755
Abstract
1-(2-Deoxy-.beta.-D-erythro-pentofuranosyl)-1H-pyrrolo-[3,2-c]pyridine (2''deoxy-3,7-dideazanebularine, 1) and 1(2-deoxy-.beta.-D-erythro-pentofuranosyl)-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (2''-deoxy-3,7-dideazainosine, 2a) have been synthesized by regio- and diastereospecific solid-liquid phase-transfer glycosylation. Employing the cryptand TDA-1, solid KOH, and an aprotic solvent the nucleoside 6 was formed in almost quantitative yield. It was converted into compounds 2b or 3b by selective displacement of the 4-chloro group. Compounds 1, 2a, or 3c were obtained after catalytic hydrogenation. The nucleoside 2a is extremely stable under acidic as well as under alkaline conditions.Keywords
This publication has 1 reference indexed in Scilit:
- Aza-indoles—IIITetrahedron, 1975