Kiliani on ketoses: branched carbohydrate building blocks from d-fructose and l-sorbose

3-O-tert-Butyldimethylsilyl-2,2′:5,6-di-O-isopropylidene-2-C-hydroxymethyl-D-1,4-gluconolactone

“…The diacetonide (1) was prepared from fructose (2) (Hotchkiss et al, 2004). The title material was crystallized from methanol as colourless plates.…”

2-C-Hydroxymethyl-2,3-O-isopropylidene-D-mannono-1,5-lactam

“…The azidolactone (5), prepared from l-sorbose, (Hotchkiss et al, 2004;Soengas et al, 2005) on hydrogenation gave an amine from which the silyl ether protecting groups were removed by treatment with tetrabutyl ammonium fluoride. The azidolactone (5), prepared from l-sorbose, (Hotchkiss et al, 2004;Soengas et al, 2005) on hydrogenation gave an amine from which the silyl ether protecting groups were removed by treatment with tetrabutyl ammonium fluoride.…”

1,5-Anhydro-2,3-O-isopropylidene-L-lyxofuranose [(1S,4S,5S,6R)-5,6-O-isopropylidene-2,7-dioxabicyclo[2.2.1]heptane-5,6-diol]

“…Branched sugar lactones may be useful as versatile intermediates in the synthesis of novel branched biologically important molecules and biopolymeric materials (Asano et al, 2000;Ichikawa & Igarashi, 1995;Ichikawa et al, 1998;Soengas et al, 2005;Hotchkiss et al, 2004Hotchkiss et al, , 2006. The Ho crossed-aldol reaction (Ho, 1979(Ho, , 1985 of lactols with formaldehyde is one of the most powerful strategies for the synthesis of these compounds.…”