A Novel Synthetic Approach to C-Glycosyl-d- and l-Alanines

Molecules

Miroslava Martinková²  Jozef Gonda²  Jana Raschmanová²  Alexandra Novodomská²  Jozef Kožíᘞk¹ 

[1] Faculty of Chemical and Food Technology, Department of Physical Chemistry, Slovak University of Technology, Radlinského 9, SK-812 37 Bratislava, Slovak Republic; E-mails:;Institute of Chemical Sciences, Department of Organic Chemistry, P. J. Šafárik University, Moyzesova 11, SK-040 01 Košice, Slovak Republic; E-mails:

关键词: C-Glycosyl amino acids;    C-Glycosyl alanine;    [3;    3]-Sigmatropic rearrangements;    Microwave irradiation;    X-ray diffraction.;   

DOI  :  10.3390/molecules13123171

来源: mdpi

【 摘 要 】

C-Glycosyl-(S)- and (R)-alanines 12a and 12b were synthesized from the known β-C-glycoside 1. The nitrogen function was introduced by aza-Claisen rearrangement of the allylic thiocyanate 7, derived from the corresponding alcohol 6. The absolute configuration of the newly created chiral carbon center (C-3) was assigned by X-ray diffraction analysis of the intermediate 3(S)-isothiocyanato-d-glycero-d-galacto-decose 8a.

【 授权许可】

CC BY   
© 2008 by the authors; licensee Molecular Diversity Preservation International, Basel, Switzerland.