2, 4??Disubstituted Pyrrolo [2, 3??d] pyrimidine α??D??and β??D??Ribofuranosides Related to 7??Deazaguanosine

…, T Soulimane, K Mersmann, T Jürgens

Index: Seela; Soulimane; Mersmann; Jurgens Helvetica Chimica Acta, 1990 ,  vol. 73,  # 7  p. 1879 - 1887

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Citation Number: 17

Abstract

Abstract Nucleobase-anion glycosylation (KOH, tris [2-(2-methoxyethoxy) ethyl] amine (TDA- 1), MeCN) of the pyrrolo [2, 3-d] pyrimidines 4a–d with 5-O-[(1, 1-dimethylethyl) dimethylsilyl]- 2, 3-O-(1-methylethylidene)-α-D-ribo-furanosyl chloride (5) gave the protected β-D- nucleosides 6a–d stereoselectively (Scheme 1). Contrary, the β-D-halogenose 8 yielded the corresponding α-D-nucleosides (9a and 9b) apart from minor amounts of the β-D-anomers ...