Crystal or low molecular mass organogel based on sugar-derived chiral pyrano[2,3-b]naphtho[1,2-e]pyrans

Organic Letters
Rina GhoshVedavati G Puranik

Abstract

[structure: see text] 2-C-Acetoxymethyl glycal derivatives reacted with beta-naphthol in the presence of InCl(3) (30 mol %) to give chiral pyrano[2,3-b]naphtho[1,2-e]pyrans in good to excellent yields via stereoselective Ferrier rearrangement-tandem cyclization. The major glucose-derived product exhibited crystal packing with C-H...O and C-H...pi (arene) interactions and the major galactose-derived product, a low molecular mass organogelator (LMOG), formed a rare type of micro tubular gel assembly in n-hexane.

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Citations

Mar 30, 2011·Beilstein Journal of Organic Chemistry·Guijun WangSherman Coleman
Mar 29, 2018·Chemical Communications : Chem Comm·Peng LiangHuawu Shao
May 20, 2009·Langmuir : the ACS Journal of Surfaces and Colloids·Guijun WangBranden Hopkinson
Mar 17, 2009·Langmuir : the ACS Journal of Surfaces and Colloids·Sang Hyuk SeoJi Young Chang
Oct 14, 2008·Journal of the American Chemical Society·Reiko OdaIvan Huc
Apr 26, 2008·Organic Letters·Koichi TanakaMino R Caira
Nov 4, 2008·Journal of the American Chemical Society·Torsten LinkerMichael Schmittel
Nov 20, 2009·Langmuir : the ACS Journal of Surfaces and Colloids·Jiaxi CuiXinhua Wan
Sep 3, 2010·Langmuir : the ACS Journal of Surfaces and Colloids·Jiaxi CuiXinhua Wan
Jan 10, 2014·Chemical Reviews·Sukumaran Santhosh BabuAyyappanpillai Ajayaghosh

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