Oxidation of methyl α-D-glucopyranoside and some related compounds catalysed by nickel peroxide

Article abstract of DOI:10.1080/07328309608005671

Nickel sulphate efficiently catalyses oxidative glycol cleavage, using sodium hypochlorite as the primary oxidant. Suspended nickel peroxide is assumed to be the active intermediate. 2,3-Butanediol was oxidised (conversion 95%) to acetate at pH <10 and 20 °C, applying a molar ratio hypochlorite: nickel:diol of 8:0.2:1. Methyl α-D-glucopyranoside was initially oxidised to disodium (R)-2-O-[(R)-carboxylato(methoxy) methyl]erythrate. Subsequently oxidation to disodium (R)-2-O-[(R)-carboxylato (methoxy)methyl]glycerate took place. ss-Cyclodextrin was preferentially oxidatively cleaved (ca. 50%) between the C(2)-C(3) carbons, although oxidation at the C(6) carbon (ca. 25%) appeared to occur as well. In contrast, maltodextrin was oxidised at the primary hydroxyl functions.

Full text of DOI:10.1080/07328309608005671

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Journal of Carbohydrate Chemistry
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Oxidation of Methyl α-D-Glucopyranoside
and Some Related Compounds Catalysed
by Nickel Peroxide
E. J.M. Mombarg a , A. Abbadi a , F. van Rantwijk a & H. van Bekkum
a
a Laboratory of Organic Chemistry and Catalysis, Delft University of
Technology , Julianalaan 136, 2628 BL, Delft, The Netherlands
Published online: 22 Aug 2006.
To cite this article: E. J.M. Mombarg , A. Abbadi , F. van Rantwijk & H. van Bekkum (1996) Oxidation
of Methyl α-D-Glucopyranoside and Some Related Compounds Catalysed by Nickel Peroxide, Journal of
Carbohydrate Chemistry, 15:5, 513-522, DOI: 10.1080/07328309608005671
To link to this article: http://dx.doi.org/10.1080/07328309608005671
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