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Methyl 2-C-allyl-2,6-anhydro-3-deoxy-4,5:7,8-di-O-isopropylidene-D-glycero- D-talo-octonate (9a), the protected alpha-allyl C-glycoside of 3-deoxy-D-manno-2-octulosonic acid (KDO), has been synthesized using a photochemically initiated radical reaction. A phenyl thioglycoside (8) was used as the substrate and allyltributyltin as the acceptor. The stereoselectivity of the reaction was 90:10 in favour of the talo-isomer (alpha-).

C-(2,3-Dihydroxypropyl)tartronic acid is a major dicarboxylic acid formed during O2-NaOH and O2-NaHCO3 treatment of cellobiose. The observation that this acid is the main reaction product after alkali treatment of ascorbic acid in O2-free medium supports the conclusion that it is formed via an aglycon moiety related to ascorbic acid. Other dicarboxylic acids from cellobiose are oxalic, tartronic, deoxytetraric, C-(hydroxymethyl)tartronic, and succinic acids. The temperature, pH and additions of iron and cobalt salts strongly influence the product composition. The formation of aldobionic acids from cellobiose parallels the formation of aldonic acid end groups during oxygen bleaching of cellulose.