Chinese Journal of Magnetic Resonance ›› 2006, Vol. 23 ›› Issue (2): 153-159.

• Articles •     Next Articles

A New Higher Carbon Sugar-Derived Amino Alcohol and Its Intermediate: Synthesis and  NMR Studies

  

  1. Department of Chemistry, Zhengzhou University, Zhengzhou 450052, China
  • Received:2005-10-26 Revised:2005-12-26 Published:2006-06-05 Online:2006-06-05
  • Supported by:

    国家自然科学基金资助项目(20472075).

Abstract:

An intermediate of higher carbon sugar-derived amino alcohol (1αS, 2αR, 3αS, 4S, 7E, 9αR, 10αR)-1, 2∶9, 10-di-O-isopropylidene-3-nitromethyl-5, 6-dideoxy-dec-7-enos-4-ulose-1, 4∶7, 10-difuranose-4, 8-pyranose) (compound 1) was synthesized from D-xylose using hetero-Diels-Alder addition followed by Henry reaction. Compound 2 (1αS, 2αR, 3αS, 4S, 7αS, 8βR, 9αR, 10αR)-1, 2∶9, 10-di-O-isopropylidene-3-aminomethyl-5, 6-dideoxy-dec-4-ulose-1, 4∶7, 10-difuranose-4, 8-pyranose) was synthesized stereoselectively by catalytic hydrogenation of compound 1. Complete assignment of 1H and 13C chemical shifts of compounds 1 and 2 was obtained by 2D NMR techniques, including 1H-1H COSY, HMQC and HMBC. ESI-MS/MS spectra of compound 1 were also measured to study its fragmentation behaviors. The structure of compound 2 was determined.

Key words: NMR, assignment, β-amino alcohols, higher carbon sugar, intermediate

CLC Number: