Synthesis of alpha-glucuronic acid and amide derivatives in the presence of a participating 2-acyl protecting group.
[reaction: see text] Participating acyl groups located at C-2 in glucosyl and related donors generally promote formation of 1,2-trans-glycosides. Reactions of some glucuronic acid donors with TMSN(3)/SnCl(4) or ROH/SnCl(4) gave only the 1,2-cis-glycoside. The stereoselectivity is consistent with participation of the C-6 group. The methodology was used for the synthesis of a Kdn2en mimetic with the alpha-configuration.
Tosin
Manuela
M
Department of Chemistry, Centre for Synthesis and Chemical Biology, Conway Institute of Biomolecular and Biomedical Research, University College Dublin, Belfield, Dublin 4, Ireland.
Murphy
Paul V
PV
D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry; D020723:Glucuronic Acid / Q000138:chemical synthesis* / Q000737:chemistry
D000577:Amides; D020723:Glucuronic Acid