91839-86-0

Upstream product

• 138-59-0 shikimic acid 
• 40983-58-2 methyl shikimate 
• 88400-34-4 (4S,5R)-4-Acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-3-oxo-cyclohex-1-enecarboxylic acid methyl ester 
• 88400-32-2 (3aR,7R,7aR)-7-(tert-Butyl-dimethyl-silanyloxy)-2-methoxy-2-methyl-3a,6,7,7a-tetrahydro-benzo[1,3]dioxole-5-carboxylic acid methyl ester 
• 88400-31-1 (3aR,7R,7aS)-7-Hydroxy-2-methoxy-2-methyl-3a,6,7,7a-tetrahydro-benzo[1,3]dioxole-5-carboxylic acid methyl ester 
• 124-63-0 methanesulfonyl chloride 
• 88400-33-3 (4R,5R)-4-Acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-cyclohex-1-enecarboxylic acid methyl ester 
• 88400-33-3 (3R,4R,5R)-4-Acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-cyclohex-1-enecarboxylic acid methyl ester 

Relevant academic research and scientific papers

Chemistry of shikimic acid derivatives. Synthesis of specyfically labeled shikimic acid at C-3 or C-4

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.

THE SYNTHESIS OF 3- AND 4-DEUTERATED SHIKIMIC ACID

The synthesis of 3-2H- and 4-2H-L-shikimic acids was accomplished starting from commercially available L-shikimic acid.