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A New Glucose: Towards Conformationally Locked Hexoses through Annulation
Author(s) -
Mehta Goverdhan,
Ramesh Senaiar S.
Publication year - 2005
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200500031
Subject(s) - annulation , chemistry , stereochemistry , moiety , intramolecular force , stereoselectivity , ring (chemistry) , diol , photooxygenation , organic chemistry , singlet oxygen , catalysis , oxygen
A new family of surface‐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 β‐glucopyranoside and α‐glucofuranoside from a common annulated trans ‐cyclohexadiene diol ( trans ‐CHD) precursor underscores 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)