Synthesis and X-ray Studies of Novel 3-C-nitromethyl-hexofuranoses
Carbohydrate Research 2014
Māris Turks, Krista Vēze, Gļebs Kiseļovs, Jevgeņija Mackeviča, Jevgeņija Lugiņina, Anatolijs Mišņovs, Dean Markovic

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.


Atslēgas vārdi
Henry reaction, 3-C-Nitromethyl-gulofuranose, 3-C-Nitromethyl-galactofuranose, Conformations, Altona–Sundaralingam pseudorotation phase angle
DOI
10.1016/j.carres.2014.03.003
Hipersaite
http://www.sciencedirect.com/science/article/pii/S0008621514000913

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, 82.-88.lpp. ISSN 0008-6215. Pieejams: doi:10.1016/j.carres.2014.03.003

Publikācijas valoda
English (en)
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