131615-77-5Relevant academic research and scientific papers
Carbohydrate-derived partners display remarkably high stereoselectivity in aldol coupling reactions
Kuo Long Yu,Handa,Tsang,Fraser-Reid
, p. 189 - 204 (2007/10/02)
Aldol condensation between 3-keto and aldehyde sugars have been studied. The enolate 3 reacts with aldehydes preferentially from the β-face to give axial C2 condensation products. However, if the reaction conditions are not controlled properly some C2 epi
A PRACTICABLE SYNTHESIS OF N-TRIFLUOROACETYL-L-DAUNOSAMINE FROM D-GlUCOSE
Crugnola, Angelo,Lombardi, Paolo,Gandolfi, Carmelo,Arcamone, Federico
, p. 395 - 400 (2007/10/02)
A synthesis of the N-trifluoroacetyl derivative of L-daunosamine, the glucidic component of adriamycin and daunomycin, two antibiotics with proved antineoplastic activity, is described starting from D-glucose, an inexpensive carbohydrate source.The synthetic sequence involves the stereoselective introduction of the C(3) amino group and the inversion at C(5), obtained by the stereospecific hydrogenation of a 5-methylenepyranose derivative, to flip from the D over the L series.
