53153-20-1

Upstream product

• 139108-82-0 7-Benzyloxymethyl-2-methylthiobicyclo<2.2.1>hept-5-ene-2-carboxylic Acid 
• 136838-55-6 (1R,2S,4S,7R)-7-Benzyloxymethyl-2-hydroxy-bicyclo[2.2.1]hept-5-ene-2-carbaldehyde oxime 
• 136838-50-1 (1R,2S,4S,7R)-7-Benzyloxymethyl-2-bromo-bicyclo[2.2.1]hept-5-ene-2-carbaldehyde 
• 139930-89-5 (1R,2S,4S,7R,S_S)-(-)-bicyclo <2.2.1> hep-7-benzyloxymethyl-5-ene-2-p-toluenesulfinyl 
• 139930-90-8 (1R,2S,4S,7R)-(-)-bicyclo <2.2.1> hept-7-benzyloxymethyl-5-ene-2-p-tolylsulfenyl 
• 3587-60-8 Benzyloxymethyl chloride 
• 121809-01-6 (-)-3-(7'-Benzyloxymethyl-bicyclo<2.2.1>hept-5'-ene-2'-carbonyl)-1,3-oxazolin-2-one 
• 139108-84-2 (1R,2R,4S,7R)-7-Benzyloxymethyl-2-methylsulfanyl-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid ethyl ester 
• 115219-37-9 Ethyl 7-Benzyloxymethylbicyclo<2.2.1>hept-5-ene-2-endo-carboxylate 
• 39939-07-6 5-(benzyloxymethyl)cyclopentadiene 
• 115219-35-7 (1R,2S,4S,7R)-7-Benzyloxymethyl-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid 
• 139930-91-9 (1S,4R,5R,7R)-7-Benzyloxymethyl-5-chloro-5-p-tolylsulfanyl-bicyclo[2.2.1]hept-2-ene 
• 133520-34-0 (1S,2S,4R,7S)-7-Benzyloxymethyl-bicyclo[2.2.1]hept-5-en-2-ol 

Downstream Products

• 83060-94-0 (1S,2R,3S)-3-Benzyloxymethyl-2-(2-phenylselanyl-ethyl)-cyclopentanol 
• 35761-79-6 (3aR,4S,6aS)-4-Benzyloxymethyl-3,3a,4,6a-tetrahydrocyclopenta[b]furan-2-one 
• 31767-37-0 6-Benzyloxymethyl-7-hydroxy-8-iodo-2-oxabicyclo<3.3.0>octan-3-one 

Relevant academic research and scientific papers

Highly Enantioselective Synthesis of a Corey Prostaglandin Intermediate

(R)-p-tolyl vinyl sulfoxide 8 was transformed into the corresponding ethoxysulfonium compound 9 which smoothly underwent reaction with 5-benzyloxymethyl-1,3-cyclopentadiene 2 to give, after basic treatment, the bicyclic sulfoxide 10 with very high de.This

Synthesis of corey lactone via highly stereoselective asymmetric diels-alder reaction

We have succeeded in a highly stereoselective asymmetric Diels-Alder reaction between a chiral acrylate 3a derived from commercially available D-pantolactone 2 and 5-benzyloxymethyl-cyclopentadiene 4 to give the adduct 5a in 94% d.e. and 79% yield for the synthesis of Corey lactone 1.

Catalytic enantioselective synthesis of a key intermediate for the synthesis of prostanoids

A route has been demonstrated for the enantioselective synthesis of prostanoids from achiral starting materials by the use of chiral catalysts of the molecular robot class.

Asymmetric microbiological Baeyer-Villiger reaction of a bridged bicyclic ketone: Divergent behaviour of its enantiomers

The bioconversion of 7-anti-benzyloxymethylbicyclo[2.2.1]hept-5-en-2-one 1 with cells of Acinetobacter calcoaceticus NCIB 9871 has been studied. Its (1R,4S,7R) enantiomer underwent a Baeyer-Villiger oxidation yielding rearranged lactone 2 (ee 85%), whereas (1S,4R,7S)-1 was reduced to alcohols 3-endo (ee 95%) and 3-exo (o.p. 89%).