Molecules 2008, 13(12), 3171-3183; doi:10.3390/molecules13123171

A Novel Synthetic Approach to C-Glycosyl-D- and L-Alanines

1,* email, 1email, 1email, 1email, 2email and 2email
Received: 16 November 2008; in revised form: 10 December 2008 / Accepted: 11 December 2008 / Published: 15 December 2008
Download PDF [410 KB, uploaded 18 June 2014]
Abstract: 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.
Keywords: C-Glycosyl amino acids; C-Glycosyl alanine; [3; 3]-Sigmatropic rearrangements; Microwave irradiation; X-ray diffraction
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Export to BibTeX |

MDPI and ACS Style

Martinková, M.; Gonda, J.; Raschmanová, J.; Novodomská, A.; Kožíšek, J.; Perasinová, L. A Novel Synthetic Approach to C-Glycosyl-D- and L-Alanines. Molecules 2008, 13, 3171-3183.

AMA Style

Martinková M, Gonda J, Raschmanová J, Novodomská A, Kožíšek J, Perasinová L. A Novel Synthetic Approach to C-Glycosyl-D- and L-Alanines. Molecules. 2008; 13(12):3171-3183.

Chicago/Turabian Style

Martinková, Miroslava; Gonda, Jozef; Raschmanová, Jana; Novodomská, Alexandra; Kožíšek, Jozef; Perasinová, Lucia. 2008. "A Novel Synthetic Approach to C-Glycosyl-D- and L-Alanines." Molecules 13, no. 12: 3171-3183.

Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert