Synthesis 2015; 47(11): 1678-1682
DOI: 10.1055/s-0034-1380413
paper
© Georg Thieme Verlag Stuttgart · New York

A Tetrahydroxycalix[4]arene Derivative with All Bridges Monosubstituted with Methoxy Groups

Norbert Itzhak
Institute of Chemistry, The Hebrew University of Jerusalem, Jerusalem­ 91904, Israel   Email: silvio.biali@mail.huji.ac.il
,
Silvio E. Biali*
Institute of Chemistry, The Hebrew University of Jerusalem, Jerusalem­ 91904, Israel   Email: silvio.biali@mail.huji.ac.il
› Author Affiliations
Further Information

Publication History

Received: 15 December 2014

Accepted after revision: 12 February 2015

Publication Date:
18 March 2015 (eFirst)

Abstract

Reduction of the carbonyl groups of tetrahydroxyketocalix[4]arene with NaBH4 in propan-2-ol, followed by heating the product to reflux in MeOH–H2SO4, yields a mixture of stereoisomers of the tetrahydroxycalix[4]arene derivative with all bridges monosubstituted by a methoxy group. To structurally characterize the compound, the mixture of isomers was derivatized by reaction with di-tert-butyl dicarbonate–DMAP. X-ray crystal structure analysis of the all-cis isomer of the product (obtained by fractional crystallization), corroborates the presence of Boc protecting groups at the lower rim (and thus underivatized OH groups in the starting material), and four methoxy groups at the bridges.

Supporting Information

 
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  • 11 CCDC-1053221 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax: +44(1223)336033; E-mail: deposit@ccdc.cam.ac.uk.