478554-61-9Relevant academic research and scientific papers
Thermal/hyperbaric heterocycloaddition of 1,4-dialkoxy-1,3-dienes: The de novo (E,Z) way to sugars
Bataille, Carole,Begin, Gautier,Guillam, Anne,Lemiegre, Loic,Lys, Caroline,Maddaluno, Jacques,Toupet, Loie
, p. 8054 - 8062 (2007/10/03)
1-(Z)-Alkoxy-4-(E)-methoxybutadiene derivatives have been reacted with ethylgyoxylate and diethyl ketomalonate under thermal or hyperbaric conditions. They provide, with a total regioselectivity and fair to total endoselectivities, the expected dihydropyranic cycloadducts. Three of those pseudoglycals have been converted in a few classical steps (deprotection, reduction, and dihydroxylation) into (racemic) allose, mannose, and gullose derivatives. The order of these three steps has a direct influence on the efficiency of the transformation and determines the stereochemistry of the final sugar.
