53153-20-1

Upstream product

• 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 
• 139108-82-0 7-Benzyloxymethyl-2-methylthiobicyclo<2.2.1>hept-5-ene-2-carboxylic Acid 
• 133520-34-0 (1S,2S,4R,7S)-7-Benzyloxymethyl-bicyclo[2.2.1]hept-5-en-2-ol 

Downstream Products

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

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

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%).

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.

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.