130464-52-7

Usage

Uses

Used in Organic Synthesis:
(2R,3S)-3-exo-methoxycarbonyl-7-oxabicyclo[2.2.1]heptane-2-exo-carboxylic acid is used as a building block in organic synthesis for its unique molecular shape and functional groups. The carboxylic acid group allows for the formation of derivatives with different properties, making it a versatile component in the creation of new compounds.
Used in Pharmaceutical Research:
In the pharmaceutical industry, (2R,3S)-3-exo-methoxycarbonyl-7-oxabicyclo[2.2.1]heptane-2-exo-carboxylic acid is used as a potential candidate for drug development due to its specific stereochemistry and constrained molecular structure. These features may contribute to its interaction with biological targets, offering opportunities for the design of novel therapeutic agents.

Upstream product

• 6118-51-0 exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride 
• 67-56-1 methanol 

Downstream Products

• 6253-21-0 3α-hydroxymethyl-7α-oxabicyclo[2.2.1]heptane-2α-carboxylic acid lactone 
• 112918-09-9 methyl 3-exo-(benzyloxycarbonylamino)-7-oxabicyclo<2.2.1>heptane-2-exo-carboxylate 
• 112918-10-2 2-exo-(benzyloxycarbonylamino)-3-endo-formyl-7-oxabicyclo<2.2.1>heptane 
• 112918-10-2 2-exo-(benzyloxycarbonylamino)-3-exo-formyl-7-oxabicyclo<2.2.1>heptane 
• 112918-11-3 ((1R,2S,3S,4S)-3-Hydroxymethyl-7-oxa-bicyclo[2.2.1]hept-2-yl)-carbamic acid benzyl ester 
• 1086106-30-0 N-{3-[(1S,2R,7S,8R)-3-(4-fluoro-benzyl)-6-hydroxy-4-oxo-11-oxa-3-aza-tricyclo[6.2.1.0^2,7]undec-5-en-5-yl]-1-methyl-1-oxo-1λ⁶-benzo[1,2,4]thiadiazin-7-yl}-methanesulfonamide 
• 1086106-54-8 (1S,2R,7S,8R)-3-(4-fluoro-benzyl)-6-hydroxy-5-(1-methyl-7-nitro-1-oxo-1λ⁶-benzo[1,2,4]thiadiazin-3-yl)-11-oxa-3-aza-tricyclo[6.2.1.0^2,7]undec-5-en-4-one 
• 1086106-55-9 (1S,2R,7S,8R)-5-(7-amino-1-methyl-1-oxo-1λ⁶-benzo[1,2,4]thiadiazin-3-yl)-3-(4-fluoro-benzyl)-6-hydroxy-11-oxa-3-aza-tricyclo[6.2.1.0^2,7]undec-5-en-4-one 
• 1086106-53-7 (1R,2S,3R,4S)-3-{(4-fluoro-benzyl)-[2-(1-methyl-7-nitro-1-oxo-1λ⁶-benzo[1,2,4]thiadiazin-3-yl)-acetyl]-amino}-7-oxa-bicyclo[2.2.1]heptane-2-carboxylic acid methyl ester 
• 1071520-79-0 methyl (1R,2S,3R,4S)-3-{[(benzyloxy)carbonyl]amino}-7-oxabicyclo[2.2.1]heptane-2-carboxylate 
• 1071521-02-2 methyl (1R,2S,3R,4S)-3-[(4-fluorobenzyl)amino]-7-oxabicyclo[2.2.1]heptane-2-carboxylate 
• 1071517-60-6 N-{3-[(1S,2R,7S,8R)-3-(4-fluoro-3-methylbenzyl)-6-hydroxy-4-oxo-11-oxa-3-aza-tricyclo[6.2.1.02,7]undec-5-en-5-yl]-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-7-yl}methanesulfonamide 
• 1071520-86-9 methyl (1R,2S,3R,4S)-3-[(4-fluoro-3-methylbenzyl)amino]-7-oxabicyclo[2.2.1]heptane-2-carboxylate 

Relevant academic research and scientific papers

Sealed tube promoted coupling of camptothecin and norcantharidin acid ester and their preliminary biological activity evaluation in vitro

A facile synthetic method was developed for the novel acid-sensitive camptothecin norcantharidin acid ester derivatives 3 in sealed tube. This method offers several advantages including high yield and simple work procedure which can be extended for the synthesis of analogs. The new synthetic compounds 3 have shown better activity against several tumor cell lines in vitro test.

A flow chemistry approach to norcantharidin analogues

Acid-ester and acid-amide norcantharidin derivatives are prepared using a 'one-pot' synthetic procedure utilizing the ThalesNano H-cube flow hydrogenator. Traditionally, rapid library generation and reaction scale up of these analogues was limited by the batch wise hydrogenation of 5,6-dehydronorcantharidin. This was resolved with the use of flow chemistry. With no associated scale up issues, a method was devised to produce norcantharidin, along with acid-ester and acid-amide analogues on any scale necessary for biological screening.

[4 + 2] Cycloadditions of rigid s-cis dienes to C60. A synchronous Diels-Alder reaction

(Matrix presented) The Diels-Alder reaction of rigid s-cis dienes with C60 occurs by a concerted mechanism, via a symmetrical transition state.

Practical and Highly Enantioselective Ring Opening of Cyclic Meso-Anhydrides Mediated by Cinchona Alkaloids

The cinchona alkaloid-mediated opening of prochiral cyclic anhydrides in the presence of methanol leading to optically active hemiesters is described. Very structurally diverse anhydrides are converted into their corresponding methyl monoesters, and either enantiomer can be obtained with up to 99% ee by using quinine or quinidine as directing additive. After the reaction, the alkaloids can be recovered almost quantitatively and reused without loss of enantioselectivity. Additionally, a catalytic protocol which permits the substoichiometric use of quinidine in the presence of easily accessible pentamethylpiperidine (pempidine) is presented.