691849-45-3Relevant academic research and scientific papers
Short and highly stereoselective total synthesis of d-ribo-configured ureido sugars
Ulgheri, Fausta,Giunta, Daniela,Spanu, Pietro
experimental part, p. 11768 - 11775 (2009/04/05)
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.
Diastereoselective synthesis of 5-(alditol-1-C-yl)-hydantoins and their use as precursors of polyhydroxylated-α-amino acids
Ulgheri, Fausta,Orrù, Gianmauro,Crisma, Marco,Spanu, Pietro
, p. 1047 - 1050 (2007/10/03)
The synthesis of 5-(alditol-1-C-yl)-hydantoin derivatives was performed via diastereoselective aldol-type addition of 1,3-dibenzyl-hydantoin to enantiopure aldehydo sugars. Starting from the D-ribo-configured 5-(alditol-1-C-yl)-hydantoin template, the synthesis of (2R,3S,4R)-3,4,5- trihydroxynorvaline was carried out.
