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Synthesis and characterization of 4,6-O-butylidene-N-(2-hydroxybenzylidene)-β-D-glucopyranosylamine: crystal structures of 4,6-O-butylidene-α-D-glucopyranose, 4,6-O-butylidene-β-D-glucopyranosylamine and 4,6-O-butylidene-N-(2-hydroxybenzylidene)-β-D-glucopyranosylamine

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Title Synthesis and characterization of 4,6-O-butylidene-N-(2-hydroxybenzylidene)-β-D-glucopyranosylamine: crystal structures of 4,6-O-butylidene-α-D-glucopyranose, 4,6-O-butylidene-β-D-glucopyranosylamine and 4,6-O-butylidene-N-(2-hydroxybenzylidene)-β-D-glucopyranosylamine
 
Creator GUDNEPPANAVAR, RAJSEKHAR
GANGADHARMATH, UMESH B
RAO, CHEBROLU P
GUIONNEAU, PHILIPPE
SAARENKETO, PAULI K
KARI RISSANEN
 
Subject characterization
molecular structure
x-ray diffraction
crystal structure
 
Description 4,6-O-Butylidene-N-(2-hydroxybenzylidene)-β-D-glucopyranosylamine was synthesized and characterized using analytical, spectral and single-crystal X-ray diffraction methods. 1H and 13C NMR studies showed the presence of the β-anomer, which has also been confirmed by the crystal structure. The molecular structure of this compound showed the presence of the tridentate ONO ligation-core. Both precursors, 4,6-O-butylidene-α-D-glucopyranose and 4,6-O-butylidene-β-D-glucopyranosylamine were characterized using single crystal X-ray diffraction. The α-anomeric nature of the former and β-anomeric nature of the latter were proposed based on 1H NMR studies and were confirmed by determining the crystal structures. In addition, the crystal structure of 4,6-O-butylidene-β-D-glucopyranosylamine revealed the C-1---N–glycosylation. In all the three molecules, the saccharide unit exhibits a 4C1 chair conformation. In the lattice, the molecules are connected by hydrogen-bond interactions. The conformation of 4,6-O-butylidene-N-(2-hydroxybenzylidene)-β-D-glucopyranosylamine is stabilized via an O–H...N, intramolecular interaction, and each molecule in the lattice interacts with three neighboring molecules through hydrogen bonds of the type O–H...O and C–H...O.
 
Publisher Elsevier
 
Date 2009-02-27T11:09:38Z
2011-11-25T18:07:35Z
2011-12-26T13:06:37Z
2011-12-27T05:54:37Z
2009-02-27T11:09:38Z
2011-11-25T18:07:35Z
2011-12-26T13:06:37Z
2011-12-27T05:54:37Z
2002
 
Type Article
 
Identifier Carbohydrate Research 337(16), 1477-1484
0008-6215
http://dx.doi.org/10.1016/S0008-6215(02)00191-X
http://hdl.handle.net/10054/813
http://dspace.library.iitb.ac.in/xmlui/handle/10054/813
 
Language en