104485-83-8

Basic information

• Product Name: 7-Oxabicyclo[2.2.1]heptane-2,3-dicarboxylic acid, monomethyl ester, (1S,2R,3S,4R)-
• CAS NO: 104485-83-8
• Molecular Formula: C9H12O5
• Molecular Weight: 200.191
• Mol File: 104485-83-8.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 7-Oxabicyclo[2.2.1]heptane-2,3-dicarboxylic acid, monomethyl ester, (1S,2R,3S,4R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 7-Oxabicyclo[2.2.1]heptane-2,3-dicarboxylic acid, monomethyl ester, (1S,2R,3S,4R)-(104485-83-8)
• EPA Substance Registry System: 7-Oxabicyclo[2.2.1]heptane-2,3-dicarboxylic acid, monomethyl ester, (1S,2R,3S,4R)-(104485-83-8)

Safety Data

• Hazardous Substances Data: 104485-83-8(Hazardous Substances Data)

Upstream product

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

Downstream Products

• 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 
• 121423-92-5 (Z)-7-((1S,2S,3S,4R)-3-Benzenesulfonylamino-7-oxa-bicyclo[2.2.1]hept-2-yl)-hept-5-enoic acid methyl ester 
• 112918-15-7 (Z)-7-((1S,2S,3S,4R)-3-Benzyloxycarbonylamino-7-oxa-bicyclo[2.2.1]hept-2-yl)-hept-5-enoic acid methyl ester 
• 121423-93-6 (-)-(5Z)-7-(3-exo-(benzenesulfonylamino)-7-oxabicyclo<2.2.1>heptan-2-endo-yl)hept-5-enoic acid 
• 121423-90-3 (+)-methyl 2-exo-(benzyloxycarbonylamino)-7-oxabicyclo<2.2.1>heptane-3-exo-carboxylate 
• 112918-13-5 [(1R,2S,4S)-3-((E)-2-Methoxy-vinyl)-7-oxa-bicyclo[2.2.1]hept-2-yl]-carbamic acid benzyl ester 
• 121423-91-4 (-)-3-exo-(benzyloxycarbonylamino)-2-endo-(formylmethyl)-7-oxabicyclo<2.2.1>heptane 
• 112918-10-2 ((1R,2S,4S)-3-Formyl-7-oxa-bicyclo[2.2.1]hept-2-yl)-carbamic acid benzyl ester 
• 6253-21-0 3α-hydroxymethyl-7α-oxabicyclo[2.2.1]heptane-2α-carboxylic acid lactone 

Relevant articles and documents

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.

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.