Synthesis and spectroscopic NMR studies of a highly stable cross-ozonide product derived from a carbohydrate system

Ozonolysis of a carbohydrate derived norbornene system afforded a stable intramolecular cross-ozonide through a stereocontrolled pathway involving a regioselective fragmentation of the primary ozonide.

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(1S,2S,3S,5R,8R,10S,11R,12R)-3-Methoxy-8-phenyl-4,7,9-trioxatetracyclo-[10.2.1.02,11.05,10]pentadec-13-ene-2-carbaldehydeC20H22O5[α]D25=+35.8 (c 8.54, CHCl3)Source of chirality: methyl α-d-glucopyranosideAbsolute configuration: (1S,2S,3S,5R,8R,10S,11R,12R)

(1S,2S,3S,5R,8R,10S,11R,12S,14R,15S,19undefined) 12-(Acetoxymethoxy)methyl-3-methoxy-8-phenyl-4,7,9,16,17,18-hexoxapentacyclo[13.2.1.02,11.02,14.05,10]octadecaneC23H28O10[α]D25=+21.5 (c 0.44, CHCl3)Source of chirality: methyl α-d-glucopyranosideAbsolute configuration: (1S,2S,3S,5R,8R,10S,11R,12S,14R,15S,19undefined)