Transient protection: efficient one-flask syntheses of protected deoxynucleosides

GS Ti, BL Gaffney, RA Jones

Index: Ti, G. S.; Gaffney, B. L.; Jones, R. A. Journal of the American Chemical Society, 1982 , vol. 104, # 5 p. 1316 - 1319

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Citation Number: 503

Abstract

Abstract: Application of the concept of transient protection to the synthesis of protected deoxynucleosides is described. The deoxynucleosides are first treated with trimethylchlorosilane in pyridine for protection of the hydroxyl groups, and then immediately reacted with an acylating agent-benzoyl chloride for la and lb and isobutyric anhydride for lc- to effect N-acylation. Hydrolysis of the trimethylsilyl groups takes a few hours in aqueous ...

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