Nickel(II)-catalysed transformations of 5-azido-5-deoxy-D-glucofuranose and of 5-azido-5-deoxy-L-idofuranose

Article abstract of DOI:10.1080/07328309808002325

Nickel(II) catalysed isomerisation reactions of C-5 modified derivatives of D-glucose as well as L-idose were investigated. 5-Azido-5-deoxy-D-glucofuranose was successfully isomerised into the corresponding D-manno epimer in good yields. Contrasting this result, in the case of the 5-modified L-idofuranose probed, no evidence for successful epimerisation at C-2 could be found. However, this sugar was quantitatively rearranged into the corresponding L-sorbopyranose. Upon extended reaction periods, the latter underwent degradation to give the coresponding 4-modified methyl L-xylonate.

Full text of DOI:10.1080/07328309808002325

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Journal of Carbohydrate Chemistry
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Nickel(II)-Catalysed Transformations of 5-
Azido-5-deoxy-d-glucofuranose and of 5-
Azido-5-deoxy-l-idofuranose
Philipp Hadwiger a , Andreas Lechner a & Arnold E. Stütz a
a Istitut für Organische Chemie , Technische Universität Graz ,
Stremayrgasse 16, A-8010, Graz, Austria
Published online: 16 Aug 2006.
To cite this article: Philipp Hadwiger , Andreas Lechner & Arnold E. Stütz (1998) Nickel(II)-Catalysed
Transformations of 5-Azido-5-deoxy-d-glucofuranose and of 5-Azido-5-deoxy-l-idofuranose, Journal of
Carbohydrate Chemistry, 17:2, 241-247, DOI: 10.1080/07328309808002325
To link to this article: http://dx.doi.org/10.1080/07328309808002325
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