16613-45-9

Upstream product

• 67-56-1 methanol 
• 108-24-7 acetic anhydride 
• 81159-05-9 Acetic acid (1R,2R,3S,4R,5S)-3,4-diacetoxy-7-oxo-6-oxa-bicyclo[3.2.1]oct-2-yl ester 
• 4372-89-8 (+/-)-methyl shikimate 
• 91758-26-8 5-O-t-butyldimethylsilyl derivative of (+/-)-methyl shikimate 
• 113409-77-1 methyl (1,3,4/2,5)-2,3,4,5-tetrahydroxy-3,4-O-isopropylidenecyclohexane-1-carboxylate 
• 113409-78-2 (3aS,4S,5R,7R,7aR)-2,2-Dimethyl-4,7-bis-(toluene-4-sulfonyloxy)-hexahydro-benzo[1,3]dioxole-5-carboxylic acid methyl ester 
• 113409-81-7 methyl DL-(1,3,4/2,5)-2,3,4,5-tetrahydroxy-2,5-di-O-p-tolylsulfonylcyclohexane-1-carboxylate 
• 113409-79-3 methyl DL-(1,3,4/2,5)-2,3,4,5-tetrahydroxy-2-O-p-tolylsulfonylcyclohexane-1-carboxylate 
• 10226-78-5 methyl DL-(1,3,4/2,5)-2,3,4,5-tetra-O-acetyl-2,3,4,5-tetrahydroxycyclohexane-1-carboxylate 
• 104731-69-3 methyl DL-(1,3,4/2,5)-2,3,4,5-tetrahydroxycyclohexane-1-carboxylate 
• 104731-68-2 methyl DL-(1,3/2)-2,3-di-O-acetyl-2,3-dihydroxy-4-cyclohexene-1-carboxylate 

Downstream Products

• 15271-51-9 (+/-)-shikimic acid 

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.