Synthesis and reactions of c-hetaryl substituted ketoses

Article abstract of DOI:10.1080/07328309708006530

O-Benzyl protected gluconolactone 1 reacts readily with 2-lithio derivatives of quinaldine, 2-methylquinoxaline, 2-methylbenzimidazole and N-protected derivatives, and 1-benzyloxymethyl-2-methylimidazole at low temperatures to afford as monoaddition products the corresponding D-gluco-2-heptuloses 2-5. The benzyl protective groups can be readily removed by hydrogenolysis as shown for the transformation of 4a into 8. Acylation reactions with 4a exhibited an interesting interplay between O-and N-acylation which is dependent on the nature of the acylating agent and on the reaction conditions. Reductive removal of the anomeric hydroxy group in 4a-c and 5 was readily performed via elimination products 18a-c and 23; their hydrogenation with Pd/C gave directly the O,N-deprotected C-β-D-glucopyranosylmethyl derivatives 21 and 25, respectively.

Full text of DOI:10.1080/07328309708006530

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Journal of Carbohydrate Chemistry
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Synthesis and Reactions of C-Hetaryl
Substituted Ketoses
Hansjörg Streicher a , Martin Reiner a & Richard R. Schmidt a
a Fakultät Chemie, Universität Konstanz , Postfach 5560 M 725
D-78434, Konstanz, Germany
Published online: 19 Aug 2006.
To cite this article: Hansjörg Streicher , Martin Reiner & Richard R. Schmidt (1997) Synthesis and
Reactions of C-Hetaryl Substituted Ketoses, Journal of Carbohydrate Chemistry, 16:3, 277-298, DOI:
10.1080/07328309708006530
To link to this article: http://dx.doi.org/10.1080/07328309708006530
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