Crystal or Low Molecular Mass Organogel Based on Sugar-Derived Chiral Pyrano[2,3-b]naphtho[1,2-e]pyrans

2-C-Acetoxymethyl glycal derivatives reacted with β-naphthol in the presence of InCl3 (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...

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Bibliographic Details
Published in:Organic letters 2006-03, Vol.8 (6), p.1061-1064
Main Authors: Ghosh, Rina, Chakraborty, Arijit, Maiti, Dilip K, Puranik, Vedavati G
Format: Article
Language:English
Subjects:
Carbohydrates - chemistry
Microscopy, Electron, Scanning
Molecular Conformation
Molecular Structure
Naphthalenes - chemistry
Pyrans - chemistry
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Summary:2-C-Acetoxymethyl glycal derivatives reacted with β-naphthol in the presence of InCl3 (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···π (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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol052963e