The synthesis of 1,7-dideaza-2'-deoxyadenosine (11 and related pyrrolo[2,3-blpyridine 2'-deoxy-B-D-ribofuranosides is described.Glycosylation of the anions of the pyrrolo[2,3-blpyridines or with 2-deoxy-3,5-di-0-(p-tolu0y1)-a-D-erythr0-pentofuranosyl chloride (61 has been carried out under phase-transfer conditions (NeCN, solid KOH, TDA-1, 25OC) and was complete within less than 15 min.The reaction was stereoselective and 8-nucleosides were formed exclusively.The position of glycosylation as well as the anomeric configuration were assigned by NOE difference spectroscopy.Compound 1 was extremely stable against acid or base and was not deaminated by adenosine deaminase.
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Seela et al. (1989) studied this question.
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