81846-56-2Relevant academic research and scientific papers
Preparation of D-galactofuranosyl nitromethanes: A revision and a new approach
Vojtech, Michal,Petru?ová, Mária,Valent, Ivan,Pribulová, Bo?ena,Petru?, Ladislav
experimental part, p. 715 - 721 (2011/05/06)
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.
A New Route to Glycofuranosyl Cyanides (2,6-Anhydroaldononitriles). Reduction of Acetylated 2,5-Anhydro-1-deoxy-1-nitroalditols with Phosphorus Trichloride
Koell, Peter,Kopf, Juergen,Wess, Doris,Brandenburg, Heinz
, p. 685 - 694 (2007/10/02)
Addition of nitromethane to D-ribose, D-xylose, and D-galactose and subsequent cyclodehydration yields the 2,5-anhydro-1-deoxy-1-nitrohexitols and -heptitols 1, 4, 7, and 10, which are suitable educts for the preparation of the glycofuranosyl cyanides 3, 6, 9, and 12 by acetylation and reduction with PCl3 in pyridine.No anomerization is observed and no participation by the neighboring vicinal acetoxy substituents is viable, thus allowing even the preparation of 1,2-cis-cyanides, like 3 and 9, syntheses which are almost unachievable by conventional methods.The structures of the described compounds were proved directly and indirectly by X-ray structural analysis of the nitromethyl derivatives 1, 4, and 7 and of the cyanide 12.
