Crystal or low molecular mass organogel based on sugar-derived chiral pyrano[2,3-b]naphtho[1,2-e]pyrans.
[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.
Ghosh
Rina
R
Department of Chemistry, Jadavpur University, Kolkata 700032, India. ghoshrina@yahoo.com
Chakraborty
Arijit
A
Maiti
Dilip K
DK
Puranik
Vedavati G
VG
D002241:Carbohydrates / Q000737:chemistry*; D008855:Microscopy, Electron, Scanning; D008968:Molecular Conformation; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry*; D011714:Pyrans / Q000737:chemistry*
D002241:Carbohydrates; D009281:Naphthalenes; D011714:Pyrans