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Publikācija: Synthesis and X-ray Studies of Novel 3-C-nitromethyl-hexofuranoses

Publication Type Scientific article indexed in SCOPUS or WOS database
Funding for basic activity Unknown
Defending: ,
Publication language English (en)
Title in original language Synthesis and X-ray Studies of Novel 3-C-nitromethyl-hexofuranoses
Field of research 1. Natural sciences
Sub-field of research 1.4 Chemical sciences
Authors Māris Turks
Krista Vēze
Gļebs Kiseļovs
Jevgeņija Mackeviča
Jevgeņija Lugiņina
Anatolijs Mišņovs
Dean Markovic
Keywords Henry reaction, 3-C-Nitromethyl-gulofuranose, 3-C-Nitromethyl-galactofuranose, Conformations, Altona–Sundaralingam pseudorotation phase angle
Abstract A practical method for the synthesis of three novel 3-C-nitromethyl-hexofuranoses is reported. The Henry reaction on a 1,2:5,6-di-O-isopropylidene-α-d-gulofuranose-derived ketone provided a 3-C-branched gulo-isomer as the sole reaction product. The dehydration–rehydration of the latter yielded an isopropylidene-protected 3-C-nitromethyl-galactofuranose. The reaction sequence can be also used for the synthesis of a 3-deoxy-3-C-nitromethyl-hexofuranose derivative with a gulo-configuration. Two of the newly obtained carbohydrate derivatives were characterized by X-ray crystallography.
DOI: 10.1016/j.carres.2014.03.003
Hyperlink: http://www.sciencedirect.com/science/article/pii/S0008621514000913 
Reference Turks, M., Vēze, K., Kiseļovs, G., Mackeviča, J., Lugiņina, J., Mišņovs, A., Markovic, D. Synthesis and X-ray Studies of Novel 3-C-nitromethyl-hexofuranoses. Carbohydrate Research, 2014, Vol.391, Iss.1, pp.82-88. ISSN 0008-6215. Available from: doi:10.1016/j.carres.2014.03.003
Additional information Citation count:
ID 18210