A short and scalable route to orthogonally O-protected 2-deoxystreptamine

SBAMW van den Broek, BWT Gruijters…

Index: Van Den Broek, Sebastiaan A. M. W.; Gruijters, Bas W. T.; Rutjes, Floris P. J. T.; Van Delft, Floris L.; Blaauw, Richard H. Journal of Organic Chemistry, 2007 , vol. 72, # 9 p. 3577 - 3580

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Citation Number: 13

Abstract

A seven-step synthesis of orthogonally O-protected 2-deoxy-streptamine has been developed from readily available neomycin, with an overall yield of 28%. Key chemical transformations include a chemoselective glycosidic bond hydrolysis and two regioselective protective group manipulations involving acetylation and deacetylation. The synthetic route is amenable to scale-up for the production of multigram quantities of enantiopure and ...