17310-94-0

Upstream product

• 1829-60-3 dimethyl 7-oxabicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate 
• 110-00-9 furan 
• 762-42-5 dimethyl acetylenedicarboxylate 
• 67-64-1 acetone 
• 1829-60-3 dimethyl 7-oxabicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate 

Downstream Products

• 19803-01-1 7-oxa-norborn-2-ene-2,3-dicarboxylic acid 
• 92474-90-3 (+/-)-2exo-methoxy-7-oxa-norbornane-2endo,3exo-dicarboxylic acid 
• 78999-09-4 (1R,2S,6R,7S)-5-(2,4,6-Trimethyl-phenyl)-3,10-dioxa-4-aza-tricyclo[5.2.1.0^2,6]dec-4-ene-2,6-dicarboxylic acid dimethyl ester 
• 53523-27-6 dimethyl 2,6-cyclohexadiene-1,2-dicarboxylate 
• 877154-46-6 C₁₉H₂₁NO 
• 877154-45-5 C₁₉H₁₇NO₃ 
• 877154-42-2 C₂₈H₂₉N₃O₃ 
• 86758-70-5 (1R,2S,5S,6R,7S)-5-Benzoyl-4-phenyl-3,10-dioxa-4-aza-tricyclo[5.2.1.0^2,6]decane-2,6-dicarboxylic acid dimethyl ester 
• 86758-71-6 (1R,2S,5R,6R,7S)-4,5-Diphenyl-3,10-dioxa-4-aza-tricyclo[5.2.1.0^2,6]decane-2,6-dicarboxylic acid dimethyl ester 
• 28871-63-8 endo-7-oxabicyclo<2.2.1>heptane-2,3-dicarboxylic acid 
• 19803-01-1 (1S,4R)-7-Oxa-bicyclo[2.2.1]hept-2-ene-2,3-dicarboxylic acid 
• 411223-74-0 4a,8a-dimethyl-(4ar,8ac)-decahydro-1t,4t-epoxido-naphthalene-6t,7t-diol 
• 78999-02-7 (1R,2S,5R,6R,7S)-4-Methyl-5-phenyl-3,10-dioxa-4-aza-tricyclo[5.2.1.0^2,6]decane-2,6-dicarboxylic acid dimethyl ester 
• 78999-02-7 (1R,2S,5S,6R,7S)-4-Methyl-5-phenyl-3,10-dioxa-4-aza-tricyclo[5.2.1.0^2,6]decane-2,6-dicarboxylic acid dimethyl ester 

Relevant academic research and scientific papers

Retro-diels-alder reaction: Possible involvement in the metabolic activation of 7-oxabicyclo[2.2.1]hepta-2(3),5(6)-diene-2,3-dicarboxylates and a phosphonate analog

A discontinuous structure-activity relationship signaled a change in mode of action and led to the discovery of a possible novel metabolic activation mechanism. The toxicity of the herbicide endothal (exo,exo-7- oxabicyclo[2.2.1]heptane-2,3-dicarboxylic acid) to mice (ip LD50 = 14 mg/kg) is attributed to the inhibition of protein phosphatase 2A (PP2A) at the cantharidin binding site. The potency is reduced by the introduction of a 2,3- or 5,6-double bond. Surprisingly, high toxicity (ip LD50's = 15-50 mg/kg) is restored in oxabicyclohepta-2(3),5(6)-dienes substituted in the 2- and 3-positions with bis(methyl carboxylate), bis(ethyl carboxylate), and diethyl phosphonate/ethyl carboxylate, whereas the dicarboxylic acid, bis(tert-butyl carboxylate), and bis(dimethyl phosphonate) are inactive. The diene adducts do not inhibit the cantharidin binding site of PP2A. Two observations provided an alternative working hypothesis that the active but not the inactive diene adducts are protoxicants: GC analyses revealed that selected bicyclic dienes readily undergo thermal dissociation by retro- Diels-Alder reactions to liberate disubstituted acetylenes; the liberated acetylenes have mouse ip LD50's of 8-25 mg/kg. Apparent exceptions to this hypothesis are that bicyclic dienes with bis(tert-butyl carboxylate) and bis(dimethyl phosphonate) substituents are not toxic, yet their corresponding acetylenes are quite toxic. These apparent anomalies are resolved by finding that only the toxic bicyclic dienes readily react with albumin and 4- nitrobenzenethiol and that their low-toxicity analogs are much less reactive. Albumin can be replaced by hemoglobin but not by myoglobin or chymotrypsin in reaction with a bicyclic diene indicating the importance of the free thiol group. Diethyl oxabicycloheptadienedicarboxylate readily reacts with GSH to give two products, which are also formed from the corresponding acetylene, identified as the cis and trans isomers of the GSH-acetylene conjugate. This is the first proposal, to our knowledge, that a retro-Diels-Alder-type reaction is involved in the metabolic activation of a toxicant.

Development of Tetrahydrofuran Chiral Synthons by Enzymatic Approach: Improved Synthesis of a Strong Agonist of Platelet Activating Factor

Bicyclic meso diester 7 was found to undergo enantioselective hydrolysis with PLE (pig liver esterase) generating the chiral monoester 8 in excellent yield with high enantiomeric excess.The chiral monoester 8 was successfully utilized in the improved synthesis of 1R-cis-THF derivative (1), a strong agonist of PAF which we previously developed. Key Words: pig liver esterase; enantioselective hydrolysis; tetrahydrofuran; chiral synthon; platelet activating factor

New bifunctional substrates for copper-catalyzed asymmetric conjugate addition reactions with trialkylaluminium

Trialfylaluminium reagents have been found to undergo a copper-catalyzed asymmetric conjugate addition (ACA) reaction with oxabicyclo[2.2.1]hepta-2,5- diene-2,3-dicarboxylates with the simultaneous creation of two stereocenters. Different types of ligands

Chiral softballs: Synthesis and molecular recognition properties

Studies on the different congeners of the softball were undertaken to explore structural variants for enantioselective encapsulation. Two different spacer elements in the monomeric subunit render the dimeric softball chiral although the monomer itself is achiral. The dimers represent capsules with dissymmetric cavities with volumes ranging from 190 to 390 A3. The cavities are distorted spheres, and asymmetric guests, such as naturally occurring terpenes, generally prefer one enantiomer of the capsule to its mirror image. The selectivities are moderate (up to 4:1). The complexation studies show that the host capsules are flexible enough to arrange themselves comfortably around a guest but still maintain enough rigidity to be influenced by the occupancy of a chiral guest. The enantiomeric capsules can interconvert (racemize) by dissociation and recombination of their subunits.

Synthese organique sous champ microondes: Premier exemple d'activation specifique en phase homogene

The rate of several Diels-Alder reactions under conventional or microwave heating are compared at the same bulk temperature. This afford the first evidence for a specific activating effect of microwaves under homogeneous conditions.