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
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Creator |
GUDNEPPANAVAR, RAJSEKHAR
GANGADHARMATH, UMESH B RAO, CHEBROLU P GUIONNEAU, PHILIPPE SAARENKETO, PAULI K KARI RISSANEN |
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Subject |
characterization
molecular structure x-ray diffraction crystal structure |
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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.
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Publisher |
Elsevier
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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 |
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Type |
Article
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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 |
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Language |
en
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