91758-39-3Relevant articles and documents
Chemistry of shikimic acid derivatives. Synthesis of specyfically labeled shikimic acid at C-3 or C-4
Zamir, Lolita O.,Luthe, Corinne
, p. 1169 - 1175 (2007/10/02)
Specifically labeled shikimic acids with tritium or deuterium at posiions C-3 or C-4 were synthesized.Commercially available L-shikimic acid was converted to its 3- and 4-ketones, after suitable protection of the hydroxyl groups at C-4, C-5 and C-3, C-5.Reduction of the 3-keto or 4-keto-shikimic acid derivatives with sodium borodeuteride and deprotection gave mostly 3-D-epi-shikimic acid or 4-D-shikimic acid.An internally assisted inversion of the 3-D-epi-shikimic acid derivative and deprotection gave 3-D-shikimic acid.