121468-33-5

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 
• 88165-26-8 methyl 3α,4α-isopropylidenedioxy-5β-hydroxycyclohex-1-ene-1-carboxylate 
• 91758-26-8 5-O-t-butyldimethylsilyl derivative of (+/-)-methyl shikimate 
• 109430-30-0 (3aS,7R,7aR)-methyl 7-hydroxy-2,2-dimethyl-3a,6,7,7a-tetrahydrobenzo[d][1,3]dioxole-5-carboxylate 
• 121388-51-0 (1S,2S,3S,4S,5S,6S)-2-Hydroxymethyl-5,6-O,O-isopropylidene-5,6-dihydroxy-3-(2-pyridylthio)-7-oxabicyclo<2.2.1>heptane 
• 88165-26-8 (+/-)-3,4-O,O-isopropylidine-1-methoxycarbonyl-3α,4α,5α-trihydroxycyclohexene 
• 83604-10-8 rac-methyl 5-hydroxycyclohexa-1,3-diene-1-carboxylate 
• 83604-10-8 (R)-5-Hydroxy-cyclohexa-1,3-dienecarboxylic acid methyl ester 
• 104731-68-2 methyl DL-(1,3/2)-2,3-di-O-acetyl-2,3-dihydroxy-4-cyclohexene-1-carboxylate 

Downstream Products

• 80631-78-3 methyl (1α,5α,6α)-5-hydroxy-8-phenyl-7,9-dioxabicyclo<4.3.0>non-3-ene-3-carboxylate 
• 16929-37-6 3-<(1-Carboxyvinyl)oxy>benzoic acid 
• 16929-33-2 methyl 3-[(3-methoxy-3-oxoprop-1-en-2-yl)oxy]benzoate 
• 83604-13-1 (4aR,8S,8aS)-3-Methylene-2-oxo-8-phenylselanyl-2,3,4a,7,8,8a-hexahydro-benzo[1,4]dioxine-6-carboxylic acid methyl ester 
• 80631-81-8 2-((3aS,4S,7aS)-6-Methoxycarbonyl-2-phenyl-3a,4,7,7a-tetrahydro-benzo[1,3]dioxol-4-yloxy)-malonic acid dimethyl ester 
• 83604-12-0 methyl (3β,4α,5β)-3--4-(benzoyloxy)-5-bromo-1-cyclohexene-1-carboxylate 
• 80657-95-0 chorismic acid 
• 80631-87-4 dimethyl chlorismate 
• 80631-86-3 (3S,4R,5R)-4-Hydroxy-3-(1-methoxycarbonyl-vinyloxy)-5-phenylselanyl-cyclohex-1-enecarboxylic acid methyl ester 
• 80631-84-1 methyl (3β,4α,5β)-3-<<1-(methoxycarbonyl)ethenyl>oxy>-4-(benzoyloxy)-5-bromo-1-cyclohexene-1-carboxylate 
• 80631-82-9 methyl (3β,4α,5β)-3--4-(benzoyloxy)-5-bromo-1-cyclohexene-1-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 
• 80631-80-7 methyl (1α,5α,6α)-5--8-phenyl-7,9-dioxabicyclo<4.3.0>non-3-ene-3-carboxylate 
• 80631-83-0 2-((1R,5S,6S)-6-Benzoyloxy-5-bromo-3-methoxycarbonyl-cyclohex-2-enyloxy)-2-dimethylaminomethyl-malonic acid dimethyl ester 

Relevant academic research and scientific papers

Synthesis of some carbahexopyranoses using Mn/CrCl3 mediated domino reactions and ring closing metathesis

An efficient and common method for the synthesis of 5a-carba-α-D-mannopyranose 5, 5a-carba-β-D-mannopyranose 6, (+) methyl shikimate 9, (+) methyl-5-epi-shikimate 10, validamine analogue 15 and valiolamine analogue 16 from D-mannose, formal synthesis of T

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,

Chiral Synthesis of (+)-Methyl 5-epi-Shikimate by Asymmetric Diels-Alder Reaction of (S)S-3-(2-Pyridylsulfinyl)acrylate

(+)-Methyl 5-epi-shikimate (9) was synthesized diastereoselectively by asymmetric Diels-Alder reaction of (S)S-3-(2-pyridylsulfinyl)acrylate (1) with furan.

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.