88400-41-3

Upstream product

• 88400-38-8 (3R,5R)-3-Acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-4-oxo-cyclohex-1-enecarboxylic acid methyl ester 
• 83604-10-8 rac-methyl 5-hydroxycyclohexa-1,3-diene-1-carboxylate 
• 69739-34-0 t-butyldimethylsiyl triflate 
• 563-63-3 silver(I) acetate 
• 90687-26-6 (+/-)-methyl-5-β-O-t-butyldimethylsilyloxycyclohexa-1,3-dienoate 
• 88400-33-3 (4R,5R)-4-Acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-cyclohex-1-enecarboxylic acid methyl ester 
• 40983-58-2 methyl shikimate 
• 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 
• 127-08-2 potassium acetate 
• 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 
• 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 
• 138-59-0 shikimic acid 

Downstream Products

• 91758-37-1 C₁₈H₂₉⁽²⁾HO₇Si 
• 88400-33-3 (3R,4R,5R)-4-Acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-cyclohex-1-enecarboxylic acid methyl ester 
• 88424-81-1 (3S,4R,5R)-4-Acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-cyclohex-1-enecarboxylic acid methyl ester 
• 88400-33-3 (3S,4S,5R)-4-Acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-cyclohex-1-enecarboxylic acid methyl ester 
• 91758-26-8 5-O-t-butyldimethylsilyl derivative of (+/-)-methyl shikimate 
• 4372-89-8 (+/-)-methyl shikimate 
• 88400-39-9 C₁₈H₂₉⁽²⁾HO₇Si 
• 91758-54-2 C₁₂H₁₅⁽²⁾HO₇ 
• 91758-39-3 (3R,4S,5R)-3,4-Diacetoxy-5-hydroxy-cyclohex-1-enecarboxylic acid methyl ester 
• 88400-40-2 <4-2H>shikimic acid 
• 138-59-0 shikimic acid 
• 91758-44-0 C₁₆H₂₇⁽²⁾HO₆Si 
• 88400-34-4 (4R,5R)-4-Acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-3-oxo-cyclohex-1-enecarboxylic acid methyl ester 
• 88400-36-6 (3R,4R,5R)-3,4-Diacetoxy-5-(tert-butyl-dimethyl-silanyloxy)-cyclohex-1-enecarboxylic acid methyl ester 

Relevant academic research and scientific papers

AN IMPROVED SYNTHESIS OF (+/-)-METHYL SHIKIMATE THROUGH STEREOSELECTIVE CIS-DIHYDROXYLATION OF (+/-)-METHYL 5β-HYDROXYCYCLOHEXA-1,3-DIENOATE UNDER PREVOST'S REACTION CONDITIONS

A Prevost-type reaction under "wet" conditions upon the O-t-butyl-dimethylsilyl derivative of (+/-)-methyl 5β-hydroxycyclohexa-1,3-dienoate gives (+/-)-methyl 3α-acetoxy-4β-hydroxy-5β-t-butyldimethylsilyloxycyclohexene which may be readily deprotected to afford (+/-)-methyl shikimate in very high yield.Less selectivity is observed in a similar reaction upon the parent alcohol and when this compound is reacted under dry conditions the major product is (+/-)-methyl 4β,5β-epoxy-3β-acetoxycyclohexenoate.An analysis of Prevost reactions with exo and endo methyl 7-oxabicyclohept-5-en-2-oate is also described.

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.