141781-68-2

Upstream product

• 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 
• 88400-41-3 (+/-)-methyl 3α-acetoxy-4β-hydroxy-5β-t-butyldimethylsilyloxycyclohexene 
• 88165-26-8 (+/-)-3,4-O,O-isopropylidine-1-methoxycarbonyl-3α,4α,5α-trihydroxycyclohexene 
• 21987-33-7 7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylic acid,methyl ester 
• 92830-74-5 (+/-)-methyl 4,5-O,O-isopropylidine-4α,5α-dihydroxycyclohexen-3-one-1-carboxylate 
• 186767-30-6 (3S,4S,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-3,4-dihydroxy-cyclohex-1-enecarboxylic acid methyl ester 
• 171963-38-5 methyl [3S-(3α,4β,5α)]-3,4,5-trihydroxy-1-cyclohexene-1-carboxylate 
• 78844-86-7 rac-(1R,5R,6S)-3-methoxycarbonyl-7-oxabicyclo[4.1.0]hept-2-en-5-ol 
• 146582-76-5 Acetic acid (3aS,7S,7aR)-7-acetoxy-5-furan-2-yl-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-4-yl ester 
• 19902-87-5 (3aS,7S,7aR)-4,7-Diacetoxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxole-5-carboxylic acid methyl ester 
• 146682-46-4 (3aR,7S,7aS)-7-(tert-Butyl-dimethyl-silanyloxy)-5-iodo-2,2-dimethyl-7,7a-dihydro-3aH-benzo[1,3]dioxol-4-one 
• 186666-50-2 3-((1S,2S,4S)-7-Oxa-bicyclo[2.2.1]hept-5-ene-2-carbonyl)-oxazolidin-2-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 
• 16613-45-9 (+/-)-methyl triacetylshikimate 
• 15271-51-9 (+/-)-shikimic acid 
• 10191-00-1 (+)-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 
• 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 

Relevant academic research and scientific papers

Synthesis of (+)- and (-)-Methyl Shikimate from Benzene

cis-Cyclohexa-3,5-diene-1,2-diol 2, the product of oxidation of benzene by mutants of Pseudomonas putida, was transformed into optically pure 4 in a sequence involving asymmetrization of meso-diol 3 in organic media with Pseudomonas cepacia lipase.Alcohol

Conversion of (-)-3-dehydroshikimic acid into derivatives of the (+)-enantiomer

(-)-3-DHS (1), a compound available in large quantity through "engineering" of the shikimic acid pathway, has been converted over eight steps into the methyl ester, ent-2, of the (+)-enantiomer. Methyl (+)-shikimate (15) and its C-3 epimer (ent-5) have al

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,

Bis(oxazoline) and bis(oxazolinyl)pyridine copper complexes as enantioselective Diels-Alder catalysts: Reaction scope and synthetic applications

The scope of the Diels-Alder reaction catalyzed by bis(oxazoline) copper complexes has been investigated. In particular, [Cu((S,S)-t-Bu-box)](SbF6)2 (1b) has been shown to catalyze the Diels-Alder reaction between 3-propenoyl- 2-oxaz

Cationic bis(oxazoline)Cu(II) Lewis acid catalysts. Enantioselective furan Diels-Alder reaction in the synthesis of ent-shikimic acid

The highly enantioselective Diels-Alder reaction between acryloyl oxazolidinone and furan, catalyzed by cationic bis(4-tert-butyloxazoline)Cu)(II) complex 1, is presented. Though the reaction equilibrates rapidly at -20°C, reaction at -78°C permits isolation of the kinetic product mixture. The synthetic utility of the reaction is demonstrated by the conversion of the cycloadduct to ent-shikimic acid.

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.

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.