Facile Synthesis of Pyrrolo[2,3-d]pyrimidine and Pyrrolo[3,2-c]pyridine 2',3'-Dideoxyribonucleosides via Nucleobase Anion Glycosylation with 2,3-Dideoxy-D-glycero-pentofuranosyl Chloride

1 January 1989

journal article
research article
Published by The Japan Institute of Heterocyclic Chemistry in HETEROCYCLES

Vol. 29 (11) , 2193-2197
https://doi.org/10.3987/com-89-5160

Abstract

A facile synthesis of pyrrolo[2,3-d]pyrimidine and pyrrolo[3,2-c]pyridine 2'',3''-dideoxyribonucleosides employing a nucleobase anion and 2,3-dideoxy-D-glycero-pentofuranosyl chloride is described. The synthetic route allows large scale preparation of 2'',3''-dideoxytubercidin, 3, 7-dideaza-2'',3''-dideoxyadenosine and related base-modified 2'',3''-dideoxyribonucleosides not accessible by conventional glycosylation techniques.

Keywords

HETEROCYCLES

This publication has 1 reference indexed in Scilit:

Stereoselective synthesis of pyrrolo[2,3‐d]pyrimidine α‐ and β‐D‐ribonucleosides from anomerically pure D‐ribofuranosyl chlorides: Solid‐Liquid Phase‐Transfer Glycosylation and ¹⁵N‐NMR Spectra
Helvetica Chimica Acta, 1988