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Glycosylamines of 4,6-O-butylidene-α-D-glucopyranose: synthesis and characterization of glycosylamines, and the crystal structure of 4,6-O-butylidene-N-(o-chlorophenyl)-β-D-glucopyranosylamine

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Title Glycosylamines of 4,6-O-butylidene-α-D-glucopyranose: synthesis and characterization of glycosylamines, and the crystal structure of 4,6-O-butylidene-N-(o-chlorophenyl)-β-D-glucopyranosylamine
 
Creator GUDNEPPANAVAR, RAJSEKHAR
RAO, CHEBROLU P
SAARENKETO, PAULI K
KOLEHMAINEN, ERKKI
KARI RISSANEN
 
Subject conformations
molecular weight
amines
synthesis (chemical)
 
Description A total of nine glycosylamines of 4,6-O-butylidene-α-D-glucopyranose were synthesized using primary amines having various groups in their ortho- or para-positions. Among these, six are monoglycosylamines, including one primary glycosylamine, and three are bis-glycosylamines. All these compounds were characterized by 1H, 1H–1H COSY, 1H–13C COSY and 13C NMR spectroscopy and FTIR spectra. The FAB mass spectra provided the molecular weights of the products by exhibiting the corresponding molecular ion peaks. The crystal structure of 4,6-O-butylidene-N-(o-chlorophenyl)-β-D-glucopyranosylamine revealed the C-1 glycosylation, the β-anomeric nature, and the 4C1 chair conformation of the saccharide unit in the product. In the lattice two types of dimers exist. While one type of dimer is formed through O–H...O type of interactions, the other type is formed via C–H...O type of interactions. In the direction of these C–H...O type of interactions, the dimeric units are connected to form a chain.
 
Publisher Elsevier
 
Date 2009-02-27T11:10:23Z
2011-11-25T18:09:36Z
2011-12-26T13:06:31Z
2011-12-27T05:54:21Z
2009-02-27T11:10:23Z
2011-11-25T18:09:36Z
2011-12-26T13:06:31Z
2011-12-27T05:54:21Z
2002
 
Type Article
 
Identifier Carbohydrate Research 337(3), 187-194
0008-6215
http://dx.doi.org/10.1016/S0008-6215(01)00311-1
http://hdl.handle.net/10054/817
http://dspace.library.iitb.ac.in/xmlui/handle/10054/817
 
Language en