Ulgheri, Fausta and Giunta, Daniela and Spanu, Pietro (2008) Short and highly stereoselective total synthesis of d-ribo-configured ureido sugars. Tetrahedron, Vol. 64 (51), p. 11768-11775. ISSN 0040-4020. Article.
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An highly stereoselective, flexible and very short synthetic approach to d-ribo-configured ureido monosaccharides of the aldose, aldonic acid and alditol series has been performed starting from the 5-(alditol-1-C-yl)-hydantoin intermediates, obtained via aldol-type addition reaction of hydantoin based building blocks to enantiomerically pure aldehydes. A study to assess the stereoselectivity of this reaction has been undertaken and a very high increase of diastereoselectivity was observed depending on the hydantoin protecting group. The imidazolidinone ring elaboration of 5-(alditol-1-C-yl)-hydantoin intermediates to give ureido sugar derivatives was studied.
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