215510-13-7Relevant articles and documents
A 2-C-fructosyl-propanone locked in a 2,7-dioxabicyclo[3.2.1]octane framework
Peters, Siegfried,Lichtenthaler, Frieder W.,Lindner, Hans J.
, p. 2475 - 2479 (2007/10/03)
Condensation of D-fructose with pentane-2,4-dione in mildly alkaline aqueous solution generates a novel sugar-based scaffold: a 2-C-fructosyl-propanone compressed by formation of a cycloacetal into a 2,7-dioxabicyclo[3.2.1]octane framework.
C-glycosides by aqueous condensation of β-dicarbonyl compounds with unprotected sugars
Riemann, Ingo,Papadopoulos, Michael A.,Knorst, Marion,Fessner, Wolf-Dieter
, p. 147 - 154 (2007/10/03)
Condensation of 1,3-diketones with unprotected aldoses in water, under mildly alkaline conditions, provides a convenient and effective route to C-glycosidic ketones in high yields. Reactions usually proceed with high β-'anomeric' stereoselectivity because product composition is determined by thermodynamic control. Mechanistically, the condensation follows a typical Knoevenagel scheme, after which an intramolecular oxa-Michael cyclization determines C-glycoside configuration by following an exo- or endo-trig pathway. With open-chain 1,3-diketones, an ensuing retro-Claisen fragmentation occurs to furnish simple glycosyl monoketones. The C-glycosides then slowly further dehydrate under the reaction conditions to give 2,5-disubstituted furans.