A1 Journal article (refereed)
Glycosylamines of 4,6-O-butylidene-a-D-glucopyranose: Synthesis and characterization of glycosylamines, and the crystal structure of 4,6-O-butylidene-N-(o-chlorophenyl)-b-D-glucopyranosylamine (2002)

Saarenketo, P., Rissanen, K., Kolehmainen, E., Rajsekhar, G., & Rao, C. P. (2002). Glycosylamines of 4,6-O-butylidene-a-D-glucopyranose: Synthesis and characterization of glycosylamines, and the crystal structure of 4,6-O-butylidene-N-(o-chlorophenyl)-b-D-glucopyranosylamine. Carbohydrate Research, 337(3), 187-194. https://doi.org/10.1016/s0008-6215(01)00311-1

JYU authors or editors

Publication details

All authors or editors: Saarenketo, Pauli; Rissanen, Kari; Kolehmainen, Erkki; Rajsekhar, Gudneppanavar; Rao, Chebrolu Pulla

Journal or series: Carbohydrate Research

Publication year: 2002

Volume: 337

Issue number: 3

Pages range: 187-194

Publication language: English

DOI: https://doi.org/10.1016/s0008-6215(01)00311-1

Publication open access: Not open

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Abstract

A total of nine glycosylamines of 4,6-O-butylidene-alpha-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)-beta-D-glucopyranosylamine revealed the C-1 glycosylation, the beta-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.

Free keywords: 4; 6-O-butylidene-N-(o-chlorophenyl)-b-D-glucopyranosylamine; synthesis; characterization; NMR; X-ray crystal structure

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Ministry reporting: Yes

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