Synthesis and Reactions of C-Hetaryl Substituted Ketoses

Streicher, Hansjorg, Reiner, Martin and Schmidt, Richard R (1997) Synthesis and Reactions of C-Hetaryl Substituted Ketoses. Journal of Carbohydrate Chemistry, 16 (3). 277 - 298.

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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-ß-D-glucopyranosylmethyl derivatives 21 and 25, respectively.

Item Type: Article
Schools and Departments: School of Life Sciences > Chemistry
Depositing User: Hans Streicher
Date Deposited: 06 Feb 2012 19:32
Last Modified: 23 Mar 2012 10:22
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