14671-74-0

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 
• 83604-10-8 rac-methyl 5-hydroxycyclohexa-1,3-diene-1-carboxylate 
• 93000-77-2 (1α,2β,4β,6α)-3,8-dioxatricyclo<4.2.1.0^2,4>nonan-7-one 
• 113409-77-1 methyl (1,3,4/2,5)-2,3,4,5-tetrahydroxy-3,4-O-isopropylidenecyclohexane-1-carboxylate 
• 83604-10-8 (R)-5-Hydroxy-cyclohexa-1,3-dienecarboxylic acid methyl ester 
• 113409-79-3 methyl DL-(1,3,4/2,5)-2,3,4,5-tetrahydroxy-2-O-p-tolylsulfonylcyclohexane-1-carboxylate 
• 91758-26-8 5-O-t-butyldimethylsilyl derivative of (+/-)-methyl shikimate 
• 88400-41-3 (+/-)-methyl 3α-acetoxy-4β-hydroxy-5β-t-butyldimethylsilyloxycyclohexene 
• 88517-55-9 (+/-)-methyl 5,6-O,O-isopropylidinecyclohexa-1,3-diene-2-carboxylate 
• 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 
• 2306-23-2 shikimic acid 

Downstream Products

• 1257516-56-5 C₁₀H₁₄O₆ 
• 1257516-57-6 C₁₀H₁₄O₆ 
• 15271-51-9 (+/-)-shikimic acid 
• 138-59-0 +/-5-epishikimic acid 
• 142945-29-7 methyl 3α,4α-hydroxy-5β-<2-methoxycarbonylprop-1-en-3-yl>-cyclohex-1-ene-1-carboxylate 
• 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 
• 80657-95-0 chorismic acid 

Relevant academic research and scientific papers

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.

Synthesis and biological evaluation of novel 4-phenylaminobenzofuro[2,3-d]pyrimidine derivatives

A series of novel 4-phenylaminobenzofuro[2,3-d]pyrimidine derivatives had been prepared and assessed for their in vitro antiproliferative activities against three lung cancer cell lines (A549, H460 and H1975). The bioassay results showed most of the desig

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,

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

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.

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.