91758-27-9

Upstream product

• 138-59-0 shikimic acid 
• 88400-33-3 (4R,5R)-4-Acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-cyclohex-1-enecarboxylic acid methyl ester 
• 91758-25-7 Methyl (3R,4R,5R)-5-<(tert-Butyl)dimethylsilyloxy>-3,4-<(methoxymethylene)dioxy>cyclohex-1-ene-1-carboxylate 
• 91758-24-6 Methyl (3R,4S,5R)-5-Hydroxy-3,4-<(methoxymethylene)dioxy>cyclohex-1-ene-1-carboxylate 
• 88400-36-6 (3R,4R,5R)-3,4-Diacetoxy-5-(tert-butyl-dimethyl-silanyloxy)-cyclohex-1-enecarboxylic acid methyl ester 
• 91758-39-3 (3R,4S,5R)-3,4-Diacetoxy-5-hydroxy-cyclohex-1-enecarboxylic acid methyl ester 
• 40983-58-2 methyl shikimate 
• 91758-26-8 Methyl (3R,4R,5R)-5-<(tert-Butyl)dimethylsilyloxy>-3,4-dihydroxycyclohex-1-ene-1-carboxylate 

Downstream Products

• 88424-81-1 (3S,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 
• 91758-37-1 C₁₈H₂₉⁽²⁾HO₇Si 

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.