187986-87-4

Upstream product

• 22627-70-9 3-ethoxycyclopent-2-en-1-one 
• 187986-85-2 (S)-3-Ethoxy-5-((S)-toluene-4-sulfinyl)-cyclopent-2-enone 

Downstream Products

• 187986-94-3 (S)-5,5-Diethoxy-3-(toluene-4-sulfonyl)-cyclopent-2-enol 
• 187986-92-1 (S)-5,5-Diethoxy-3-((R)-toluene-4-sulfinyl)-cyclopent-2-enol 
• 187986-91-0 (1S,4S,5R)-2,2-Diethoxy-4-((S)-toluene-4-sulfinyl)-6-oxa-bicyclo[3.1.0]hexane 
• 187986-90-9 (1S,2R,5S)-3,3-Diethoxy-2-iodo-5-((S)-toluene-4-sulfinyl)-cyclopentanol 

Relevant academic research and scientific papers

Sulfoxide-mediated asymmetric synthesis of glycosidase inhibitor precursors

The highly diastereoselective DIBALH and DIBALH/ZnBr2 reduction of enantiomerically pure (5S,(S)S)-3-ethoxy-5-(p-tolylsulfinyl)cyclopentenone (9)is used as a key step to the synthesis of oxazolidinone 2, a precursor of glycosidase inhibitor mannostatin. Compound 9 was obtained from 3-ethoxycyclopentenone by direct sulfinylation with (S)-N-benzyl-N-(p-tolylsulfinyl)propionamide.