4372-89-8

Upstream product

• 64-19-7 acetic acid 
• 78844-86-7 (1S,6R)-5-Hydroxy-7-oxa-bicyclo[4.1.0]hept-2-ene-3-carboxylic acid methyl ester 
• 78844-86-7 rac-(1R,5R,6S)-3-methoxycarbonyl-7-oxabicyclo[4.1.0]hept-2-en-5-ol 
• 67-56-1 methanol 
• 83693-70-3 (1α,2β,4β,5α,6α)-5-hydroxy-3,7-dioxatricyclo<4.2.1.0^2,4>nonan-8-one 
• 88517-55-9 (+/-)-methyl 5,6-O,O-isopropylidinecyclohexa-1,3-diene-2-carboxylate 
• 83604-10-8 rac-methyl 5-hydroxycyclohexa-1,3-diene-1-carboxylate 
• 88400-41-3 (+/-)-methyl 3α-acetoxy-4β-hydroxy-5β-t-butyldimethylsilyloxycyclohexene 
• 83604-10-8 (R)-5-Hydroxy-cyclohexa-1,3-dienecarboxylic acid methyl ester 
• 88165-26-8 methyl 3α,4α-isopropylidenedioxy-5β-hydroxycyclohex-1-ene-1-carboxylate 
• 91758-26-8 5-O-t-butyldimethylsilyl derivative of (+/-)-methyl shikimate 
• 113409-79-3 methyl DL-(1,3,4/2,5)-2,3,4,5-tetrahydroxy-2-O-p-tolylsulfonylcyclohexane-1-carboxylate 
• 113409-81-7 methyl DL-(1,3,4/2,5)-2,3,4,5-tetrahydroxy-2,5-di-O-p-tolylsulfonylcyclohexane-1-carboxylate 
• 93000-77-2 (1α,2β,4β,6α)-3,8-dioxatricyclo<4.2.1.0^2,4>nonan-7-one 

Downstream Products

• 80631-78-3 methyl (1α,5α,6α)-5-hydroxy-8-phenyl-7,9-dioxabicyclo<4.3.0>non-3-ene-3-carboxylate 
• 1257516-56-5 C₁₀H₁₄O₆ 
• 1257516-57-6 C₁₀H₁₄O₆ 
• 15271-51-9 (+/-)-shikimic acid 
• 142945-29-7 methyl 3α,4α-hydroxy-5β-<2-methoxycarbonylprop-1-en-3-yl>-cyclohex-1-ene-1-carboxylate 
• 138-59-0 +/-5-epishikimic acid 
• 16613-45-9 (+/-)-methyl triacetylshikimate 
• 80631-83-0 2-((1R,5S,6S)-6-Benzoyloxy-5-bromo-3-methoxycarbonyl-cyclohex-2-enyloxy)-2-dimethylaminomethyl-malonic acid dimethyl ester 
• 80631-80-7 methyl (1α,5α,6α)-5--8-phenyl-7,9-dioxabicyclo<4.3.0>non-3-ene-3-carboxylate 
• 80631-79-4 2-Hydroxy-2-((3aR,4R,7aR)-6-methoxycarbonyl-2-phenyl-3a,4,7,7a-tetrahydro-benzo[1,3]dioxol-4-yloxy)-malonic acid dimethyl ester 
• 80631-82-9 methyl (3β,4α,5β)-3--4-(benzoyloxy)-5-bromo-1-cyclohexene-1-carboxylate 
• 80631-84-1 methyl (3β,4α,5β)-3-<<1-(methoxycarbonyl)ethenyl>oxy>-4-(benzoyloxy)-5-bromo-1-cyclohexene-1-carboxylate 
• 80631-86-3 (3S,4R,5R)-4-Hydroxy-3-(1-methoxycarbonyl-vinyloxy)-5-phenylselanyl-cyclohex-1-enecarboxylic acid methyl ester 
• 80631-87-4 dimethyl chlorismate 

Relevant academic research and scientific papers

Lipase-catalyzed enantio- and regioselective transformation of 3-epi-shikimic acid derivatives as the key step for the entry of polyoxygenated carbacycles

Candida antarctica lipase B (Novozym 435)-catalyzed transesterification on methyl (±)-3,4-di-O-acetyl-5-O-(tert-butyldimethyl)silyl-3-epi-shikimate worked highly regio- and enantioselective manner. Only (3R,4S,5S)-isomer reacted with an E value over 500,

BRIEF SYNTHESES OF (+/-)-METHYL SHIKIMATE, (+/-)-METHYL EPISHIKIMATE AND STRUCTURAL VARIANTS

Two brief syntheses of (+/-)-methyl shikimate are described in a strategy which offers potentially flexible access to a range of analogues.New intramolecular rearrangement reactions of epoxides derived from methyl 7-oxabicyclohept-3-ene 6-carboxylate and methyl bicyclohept-3-ene 6 carboxylate are described.

SHIKIMIC ACIDS FROM FURAN; METHODS OF STEREOCONTROLLED ACCESS TO 3,4,5-TRIOXIGENATED CYCLOHEXENES

Oxabicycloheptenes 1 and 2 are converted to 3,4,5-oxigenated cyclohexenes by stereocontrolled hydroxylations and epoxidations coupled with reverse-Michael cleavage of the oxabicyclo system.Three epimers of shikimic acid are synthesized by these methods.

COMPLEMENTARY SHORT SYNTHESES OF (+/-)-METHYL SHIKIMATE

Two syntheses of (+/-)-methyl shikimate from the adduct of furan and methyl acrylate are described.One requires the regioselective hydroxylation of (+/-)-5β,6β-dihydroxy-O,O-isopropylidene-2-methoxycarbonylcyclohexa-1,3-diene and the other cis-dihydroxyla

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.

BRIEF DIELS ALDER SYNTHESIS OF (+/-)-METHYL 5-EPISHIKIMATE AND (+/-)-METHYL CIS-3,4-DIHYDRO-3,4-DIHYDROXYBENZOATE

Base-catalysed ring opening of the acetonide of cis-exo-2,3-dihydroxy-6-methoxycarbonyl-7-oxabicycloheptane affords a stereo-controlled route to (+/-)-methyl 5-epishikimate and thence, by an elimination process, to (+/-)-methyl-cis-3,4-dihydro-3,4-dihydroxybenzoate.