Highly stereoselective synthesis and structural characterization of new amino sugar derivatives

作者：Liu FW; Yan L; Zhang JY; Liu HM^*

来源：Carbohydrate Research, 2006, 341(3): 332-338.

DOI：10.1016/j.carres.2005.11.019

• 1,4 : 3,6-dianhydro-D-fructose
• isomannide
• amino sugar
• vicinal amino alcohols
• X-ray crystallographic study

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 FIRMS, H-1 NMR, C-13 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.

• 出版日期2006-2-27
• 单位郑州大学