Highly stereoselective synthesis and structural characterization of new amino sugar derivatives.
2-C-Nitroalkyl-1,4:3,6-dianhydromannitols were synthesized via a Henry reaction of nitroalkyls with 1,4:3,6-dianhydrofructose. Catalytic hydrogenation then afforded the corresponding vicinal amino alcohols. Oximation of 1,4:3,6-dianhydrofructose with hydroxylamine, followed by hydrogenation, gave 2-amino-1,4:3,6-dianhydro-2-deoxymannitol. All compounds were elucidated by their HRMS, 1H NMR, 13C NMR, and IR spectra. The absolute configurations of the amino sugar derivatives were confirmed by single-crystal X-ray analysis or NOESY spectral studies. The possible mechanism for hydrogenation of the nitro 2-C-nitroalkyl sugar is proposed. The conformations of the fused furan rings of nitro and amino sugar derivatives are presented.
Liu
Feng-Wu
FW
School of Pharmaceutical Sciences, New Drug Research and Development Center, Zhengzhou University, Zhengzhou 450052, PR China.
Yan
Lin
L
Zhang
Jing-Yu
JY
Liu
Hong-Min
HM
D000606:Amino Sugars / Q000138:chemical synthesis* / Q000737:chemistry*; D002236:Carbohydrate Conformation; D018360:Crystallography, X-Ray; D006860:Hydrogen Bonding; D008353:Mannitol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D008958:Models, Molecular; D019906:Nuclear Magnetic Resonance, Biomolecular; D013237:Stereoisomerism
D000606:Amino Sugars; D008353:Mannitol