Preparation of D-galactofuranosyl nitromethanes: a revision and a new approach.

Michal Vojtech, Mária Petrušová, Ivan Valent, Božena Pribulová, Ladislav Petruš

Institute of Chemistry, Center for Glycomics, GLYCOMED, Slovak Academy of Sciences, SK-84538 Bratislava, Slovakia.

Carbohydrate research 2011 May 1

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Sodium methoxide-promoted methanolysis of 7-deoxy-7-nitro-L-glycero-L-galacto-heptitol peracetate rapidly and nearly quantitatively accumulates 7-deoxy-6-O-methyl-7-nitro-L-glycero-L-galacto-heptitol. The prolonged treatment then provides 76% of D-galactofuranosyl nitromethanes and finally results in the equilibrium of 77% of β-D-galactopyranosyl nitromethane and 7-9% of three other tautomeric D-galactosyl nitromethanes. Thermal treatment of 7-deoxy-7-nitro-L-glycero-L-galacto-heptitol in boiling water peaks at a 58% content of D-galactofuranosyl nitromethanes and ends in a similar equilibrium mixture of four D-galactosyl tautomers. The relevant kinetic parameters of the latter transformation are determined by a curve fitting using the nonlinear least-squares Marquardt-Levenberg algorithm. Copyright © 2011 Elsevier Ltd. All rights reserved.

Citation

Michal Vojtech, Mária Petrušová, Ivan Valent, Božena Pribulová, Ladislav Petruš. Preparation of D-galactofuranosyl nitromethanes: a revision and a new approach. Carbohydrate research. 2011 May 1;346(6):715-21