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A new glucose: Towards conformationally locked flexoses through annulation

Mehta, G and Ramesh, SS (2005) A new glucose: Towards conformationally locked flexoses through annulation. In: European Journal of Organic Chemistry, 2005 (11). pp. 2225-2238.

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A new family of surf ace-modified carbohydrates with locked, axial-rich conformations and bipolarofacial architectures has been developed with the aid of carbocyclic ring annulation. These novel trans-decalin-based carbohydrates have been synthesized, from simple aromatic precursors such as tetralin, through the ozonolysis of an appropriately protected allylic alcohol, followed by a cascade of intramolecular acetalizations to generate the sugar pyran moiety. The stereoselective synthesis of (racemic) cyclohexane-annulated 0-glucopyranoside and a-glucofuranoside from a common annulated trans-cyclohexadiene diol (trans-CHD) precursor under-scores the versatility of our approach. The efficacy of the annulation stratagem in generating carbohydrate diversity has been demonstrated through the synthesis of two regioisomeric annulated gulose derivatives, which differ only in the site of ring annulation on the sugar moiety. The mapping of the MLP surface and solid-state architecture of the new sugar shows that cycloalkane annulation results in surface modification and fine-tuning of sugar hydrophilicity. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005).

Item Type: Journal Article
Publication: European Journal of Organic Chemistry
Publisher: John Wiley and Sons
Additional Information: Copyright of this article belongs to John Wiley and Sons.
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 08 Jun 2010 08:51
Last Modified: 19 Sep 2010 06:00
URI: http://eprints.iisc.ac.in/id/eprint/27197

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