Synthesis and X-ray studies of novel 3-C-nitromethyl-hexofuranoses.
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.
Faculty of Material Science and Applied Chemistry, Riga Technical University, 3 P. Valdena Str., Riga LV-1007, Latvia. Electronic address: maris_turks@ktf.rtu.lv.
Māris
M
Turks
Faculty of Material Science and Applied Chemistry, Riga Technical University, 3 P. Valdena Str., Riga LV-1007, Latvia.
Krista
K
Vēze
Latvian Institute of Organic Synthesis, 21 Aizkraukles Str., Riga LV-1006, Latvia.
Gļebs
G
Kiseļovs
Faculty of Material Science and Applied Chemistry, Riga Technical University, 3 P. Valdena Str., Riga LV-1007, Latvia.
Jevgeņija
J
Mackeviča
Faculty of Material Science and Applied Chemistry, Riga Technical University, 3 P. Valdena Str., Riga LV-1007, Latvia.
Jevgeņija
J
Lugiņina
Latvian Institute of Organic Synthesis, 21 Aizkraukles Str., Riga LV-1006, Latvia.
Anatoly
A
Mishnev
Department of Biotechnology, University of Rijeka, Trg braće Mažuranića 10, 51000 Rijeka, Croatia.
Dean
D
Marković
D018360:Crystallography, X-Ray; D006601:Hexoses / Q000138:chemical synthesis* / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D009574:Nitro Compounds / Q000138:chemical synthesis* / Q000737:chemistry*
D006601:Hexoses; D009574:Nitro Compounds
3-C-Nitromethyl-galactofuranose; 3-C-Nitromethyl-gulofuranose; Altona–Sundaralingam pseudorotation phase angle; Conformations; Henry reaction